Methanol → HCID 23249620, compound

HRID 658961Notes

Reaction equation

HRID 658961 reaction equation
[O:1]([CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[C:14](\[CH3:20])/[C:15](OCC)=[O:16])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.CO.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[O:1]([CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[C:14](\[CH3:20])/[CH2:15][OH:16])[Si:2]([C:5]([CH3:7])([CH3:8])[CH3:6])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 62649Sodium sulfate decahydrateHCID 11055704(E)-ethyl 7-(tert-butyldimethylsiloxy)-2-methyl-2-heptenateHCID 21273587HCID 21273587, compound

Product 1

HCID 23249620HCID 23249620, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride solution (200 ml) of Ester 4 (15.84 g; 0.0528 mol), a 0.95 M diisobutylaluminiumhydride-hexane solution (139 ml; 0.132 mol) is added at 0° C. and the whole is stirred for 1 hour. After stirring, methanol (7 ml; 0.160 mol) and sodium sulfate decahydrate (68.0 g; 0.211 mol) are added thereto and the whole is stirred at room temperature for 30 min. Sodiumsulfatedecahydrate is filtered using Chloroform (21), and the solvent is distilled off under reduced pressure to produce Alcohol 5 (13.60 g; 0.0528 mol) of 100% in yield.

Workup

  1. stirringAfter stirring
  2. stirringthe whole is stirred at room temperature for 30 min
  3. filtrationSodiumsulfatedecahydrate is filtered
  4. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-40b47e8a91e14055884f7acca915c8ef
Source dataset
uspto-grants-2011_12
Patent number
USRE043038E1

Reaction notes

Loading…