gamma-Butyrolactone methacrylate → 1-Methylcyclopentyl methacrylate

HRID 1910375Notes

Reaction equation

HRID 1910375 reaction equation
[C:1]([O:6][CH:7]1[CH:14]2[CH2:15][CH:10]3[CH2:11]C(C[C:8]1(C(C)C)C3)C2)(=[O:5])[C:2]([CH3:4])=[CH2:3].C(OC1(C)CCCC1)(=O)C(C)=C.C(OC1CCOC1=O)(=O)C(C)=C.[C:44]([O:49][CH:50]1[CH2:58][CH:57]2[O:59][CH:51]1[CH:52]1[CH:56]2[C:55](=[O:60])[O:54][CH2:53]1)(=[O:48])[C:45]([CH3:47])=[CH2:46].[C:61]([O:66][C:67]12[CH2:76][CH:71]3[CH2:72][CH:73]([CH2:75][C:69]([OH:77])([CH2:70]3)[CH2:68]1)[CH2:74]2)(=[O:65])[C:62]([CH3:64])=[CH2:63]>O1CCCC1>[C:1]([O:6][C:7]1([CH3:8])[CH2:14][CH2:15][CH2:10][CH2:11]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:44]([O:49][CH:50]1[CH2:58][CH:57]2[O:59][CH:51]1[CH:52]1[CH:56]2[C:55](=[O:60])[O:54][CH2:53]1)(=[O:48])[C:45]([CH3:47])=[CH2:46].[C:61]([O:66][C:67]12[CH2:74][CH:73]3[CH2:72][CH:71]([CH2:70][C:69]([OH:77])([CH2:75]3)[CH2:68]1)[CH2:76]2)(=[O:65])[C:62]([CH3:64])=[CH2:63]

Participants

8

Reactant 5

HCID 11206014gamma-Butyrolactone methacrylateHCID 118565233-Hydroxy-1-methacryloyloxyadamantaneHCID 155392071-Methylcyclopentyl methacrylateHCID 221688401-Oxooctahydro-4,7-epoxyisobenzofuran-5-yl methacrylateHCID 668625631-Isopropyl-adamantanyl methacrylate

Product 2

HCID 155392071-Methylcyclopentyl methacrylateHCID 131731070Odotma hama

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A control photoresist polymer (Polymer 2) was prepared according to a procedure similar to the following procedure. A solution of 1-isopropyl-adamantanyl methacrylate (IPAMA) (20 mmol), 1-methylcyclopentyl methacrylate (MCPMA) (20 mmol), 2-oxo-tetrahydro-furan-3-yl methacrylate (α-GBLMA) (30 mmol), 3-oxo-4,10-dioxa-tricyclo[5.2.1.02,6]dec-8-yl methacrylate (ODOTMA) (20 mmol), and 3-hydroxy-adamantanyl methacrylate (HAMA) (10 mmol) dissolved in 30 g of tetrahydrofuran (THF) is degassed by bubbling with nitrogen and charged to a 500 ml flask equipped with a condenser, nitrogen inlet and mechanical stirrer, along with an additional 10 g of degassed THF. The solution is brought to reflux, and 5 g of dimethyl-2,2-azodiisobutyrate is dissolved in 5 g of THF and charged in to the flask. The polymerization mixture is then stirred for about 4 hours at reflux, after which time the reaction is diluted with 5 g of THF and the polymerization mixture cooled to room temperature. The polymer is precipitated by addition to 1.0 L of isopropanol, collected by filtration, re-precipitated by dissolving in 50 g THF and addition to another 1.0 L isopropanol, and collected and dried under vacuum at 45° C. for 48 h. to yield the polymer poly(IAMA/MCPMA/α-GBLMA/ODOTMA/HAMA) (20/20/30/20/10). Mw=9,000.

Workup

  1. customA control photoresist polymer (Polymer 2) was prepared
  2. customis degassed
  3. customby bubbling with nitrogen
  4. additioncharged to a 500 ml flask
  5. customequipped with a condenser, nitrogen inlet and mechanical stirrer, along with an additional 10 g of degassed THF
  6. temperatureto reflux
  7. dissolution5 g of dimethyl-2,2-azodiisobutyrate is dissolved in 5 g of THF
  8. additioncharged in to the flask
  9. temperatureat reflux
  10. additionafter which time the reaction is diluted with 5 g of THF
  11. customThe polymer is precipitated by addition to 1.0 L of isopropanol
  12. filtrationcollected by filtration
  13. customre-precipitated
  14. dissolutionby dissolving in 50 g THF
  15. additionaddition to another 1.0 L isopropanol
  16. customcollected
  17. customdried under vacuum at 45° C. for 48 h.

Sources & evidence

ORD record
ord-050a96e184a74d11be2deb366fadb403
Source dataset
uspto-grants-2013_12
Patent number
US08603728B2

Reaction notes

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