Water → HCID 69049493, compound

HRID 1821544Notes

Reaction equation

HRID 1821544 reaction equation
[CH2:1]([O:8][C@H:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]CC=C)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:20]([OH:24])([CH3:23])([CH3:22])C.S(OS([O-])=O)([O-])=[O:26].[Na+].[Na+]>CCCCCC.C(OCC)(=O)C>[CH2:1]([O:8][C@@H:9]([CH3:10])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:22][C@@H:20]([OH:24])[CH2:23][OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 24346Disodium disulfiteHCID 69046728HCID 69046728, compound

Product 1

HCID 69049493HCID 69049493, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

A vigorously stirred solution of 6.0 g (24.3 mmol) (S)-2-benzyloxydec-9-ene in 300 ml of a 1:1 mixture of water and tert-butanol was cooled to −10° C. After addition of 29.2 g AD-Mix β (i.e. 1.2 g per mmol alkene) the mixture was stirred at 4° C. for 40 h. Subsequently, 30.0 g (158 mmol) sodium disulfite were added, and the mixture was stirred at 20° C. for another hour. The brownish suspension was extracted three times with 250 ml ethyl acetate. The organic layers were combined, dried over magnesium sulphate, and concentrated in vacuo. Flash chromatography (ethyl acetate and hexane 1:1) furnished 4.2 g (15 mmol, 62%) (2R,9S)-9-benzyloxydecan-1,2-diol as a colorless oil.

Workup

  1. stirringthe mixture was stirred at 20° C. for another hour
  2. extractionThe brownish suspension was extracted three times with 250 ml ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e8db12f395246438db0a2cbbc2c6186
Source dataset
uspto-grants-2009_10
Patent number
US07608254B2

Reaction notes

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