Methanol → HCID 15712257, compound

HRID 2294558Notes

Reaction equation

HRID 2294558 reaction equation
[C:1]([C:4]1[CH:15]=[CH:14][C:7]([C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO.C1COCC1.[BH4-].[Na+]>O>[OH:3][CH:1]([C:4]1[CH:15]=[CH:14][C:7]([C:8]([O:10][CH2:11][CH:12]=[CH2:13])=[O:9])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 21474599HCID 21474599, compound

Product 1

HCID 15712257HCID 15712257, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.1 g (15 mmol) of the allyl ester obtained above in (a), 20 ml of methyl alcohol and 20 ml of THF are introduced into a round-bottomed flask. While cooling in an icebath, 285 mg (7.5 mmol) of sodium borohydride are added in small portions and the mixture is stirred at room temperature for one hour. The reaction medium is poured into water, the mixture is extracted with ethyl ether and the organic phase is separated after settling has taken place, then dried over magnesium sulphate and evaporated. 3.1 g (100%) of the expected product are collected in the form of a colorless oil.

Workup

  1. additionare introduced into a round-bottomed flask
  2. additionare added in small portions
  3. extractionthe mixture is extracted with ethyl ether
  4. customthe organic phase is separated after settling
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. custom3.1 g (100%) of the expected product are collected in the form of a colorless oil

Sources & evidence

ORD record
ord-d881ada2f86d4e69902f2b24ce47c5bb
Source dataset
uspto-grants-1997_11
Patent number
US05688817

Reaction notes

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