Dichloromethane → HCID 57771449, compound

HRID 2070586Notes

Reaction equation

HRID 2070586 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH:6]([OH:26])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH2:20][CH2:19][CH2:18][C:17]3([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:16]=2)=[CH:9][CH:8]=1)[CH3:2].[CH:28](N(CC)C(C)C)(C)[CH3:29].ClCCl.F[B-](F)(F)F.C([O+](CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH:6]([O:26][CH2:28][CH3:29])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH2:20][CH2:19][CH2:18][C:17]3([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[CH:16]=2)=[CH:9][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 2723982Triethyloxonium tetrafluoroborateHCID 577714753-Hydroxy-3-[4-(spiro[5.5]undec-1-en-2-ylmethoxy)-phenyl]-propionic acid ethyl ester

Product 1

HCID 57771449HCID 57771449, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-hydroxy-3-[4-(spiro[5.5]undec-1-en-2-ylmethoxy)-phenyl]-propionic acid ethyl ester (4.98 g) obtained in Step 7 and N,N-diisopropylethylamine (6.97 mL) in chloroform (100 mL) was added dropwise a 1M dichloromethane solution of triethyloxonium tetrafluoroborate (20 mL) under ice-cooling over 5 minutes, followed by stirring the reaction mixture under ice-cooling for 10 minutes and then at room temperature for 2.5 hours. Then, the reaction mixture was concentrated and the residue was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio) 1:5) to give 3-ethoxy-3-[4-(spiro[5.5]undec-1-en-2-ylmethoxy)-phenyl]-pr opionic acid ethyl ester (2.175 g).

Workup

  1. temperaturecooling over 5 minutes
  2. temperaturecooling for 10 minutes
  3. concentrationThen, the reaction mixture was concentrated
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed successively with water and saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio) 1:5)

Sources & evidence

ORD record
ord-42546814af064266b373bb2abe87dfcc
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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