Phthalimide → 2-[4-(1-Hydroxy-1-methyl-ethyl)-cyclohex-1-enylmethyl]-isoindole-1,3-dione

HRID 844023Notes

Reaction equation

HRID 844023 reaction equation
O[CH2:2][C:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:12])([CH3:11])[CH3:10])[CH2:5][CH:4]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[OH:12][C:9]([CH:6]1[CH2:7][CH2:8][C:3]([CH2:2][N:17]2[C:13](=[O:23])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16]2=[O:18])=[CH:4][CH2:5]1)([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 1106624-(2-Hydroxy-2-propyl)cyclohexene-1-methanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 226124142-[4-(1-Hydroxy-1-methyl-ethyl)-cyclohex-1-enylmethyl]-isoindole-1,3-dioneYield 55.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(4-Hydroxymethyl-cyclohex-3-enyl)-propan-2-ol (5.765 grams, 34.270 mmole), Phthalimide (6.50 grams, 44.208 mmole), and triphenyl phosphene (11.60 grams, 44.208 mmole) in tetrahydrofuran (200 ml) at room temperature was added DIAD (9.010 grams, 44.552 mmole) dropwise, and the peach mixture was stirred at room temperature over night. The mixture was quenched with 150 ml water and extracted with 2×100 ml ethyl acetate. It was then concentrated to a yellow residue. This was taken up in diethyl ether, diluted with hexane, chilled and filtered. The crude product was purified via flash chromatography on silica using 50% ethyl acetate/hexane as eluent to give a yellow gum (5.73 g). MW 299.373; MS (m/e) 279 (M+−18).

Workup

  1. customThe mixture was quenched with 150 ml water
  2. extractionextracted with 2×100 ml ethyl acetate
  3. concentrationIt was then concentrated to a yellow residue
  4. additiondiluted with hexane
  5. temperaturechilled
  6. filtrationfiltered
  7. customThe crude product was purified via flash chromatography on silica using 50% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-90fabebd120143ff8d9101f58c85aa20
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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