Hydroxide → HCID 11019539, compound

HRID 1376478Notes

Reaction equation

HRID 1376478 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[CH2:11][CH:10]=[CH:9][CH2:8][C@@H:7]1[CH2:12][O:13]C(=O)C)(=[O:3])[CH3:2].P([O-])([O-])([O-])=O.[OH-].[Na+].[OH-]>>[C:1]([O:4][CH2:5][C@@H:6]1[CH2:11][CH:10]=[CH:9][CH2:8][C@@H:7]1[CH2:12][OH:13])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 961HydroxideHCID 1061PhosphateHCID 14798Sodium HydroxideHCID 11085488HCID 11085488, compound

Product 1

HCID 11019539HCID 11019539, compound

Procedure

A suspension of cis-1,2-diacetoxymethylcyclohex-4-ene (10 mmol), pH 7 phosphate buffer (25 mL) porcine pancreatic lipase (200 mg, Sigma Type II) was vigorously stirred. The reaction was kept constant by addition of 1M sodium hydroxide from a pH controller and syringe pump. After 16 hours addition of 1 eq hydroxide was complete and the mixture was filtered through a pad of Celite. The Celite was washed with ether and the filtrates were washed with ether (×3). The combined ether washes were washed with brine, dried and concentrated to yield the desired compound as a slightly yellow oil.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. washThe Celite was washed with ether
  3. washthe filtrates were washed with ether (×3)
  4. washThe combined ether washes were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5a604fd5d42543e3b7bcc3d4ce50368b
Source dataset
uspto-grants-1997_09
Patent number
US05663175

Reaction notes

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