HCID 15003275, compound → HCID 15003276, compound

HRID 1199849Notes

Reaction equation

HRID 1199849 reaction equation
C(C([O:7][CH2:8][CH2:9][CH:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:11])=O)(C)(C)C.C[O-].[Na+].CO>CO>[O:12]([CH:10]([CH3:11])[CH2:9][CH2:8][OH:7])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 15003275HCID 15003275, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 15003276HCID 15003276, compoundYield 109.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4.32 g (17.3 mmol) of pivaloyl ester 26 (prepared in 30-(2)) in 90 ml of dry methanol is added 17.3 ml (17.3 mmol) of 1M sodium methoxide-methanol solution and the mixture is stirred at 55° C. for 9 hours. After cooling, 35 g of ion exchange resin IRC-50 is added and the mixture is stirred for 20 minutes. The ion exchange resin is filtrated off and the filtrate is evaporated under reduced pressure to give 3.15 g of the crude desired alcohol 27 as an oil, which is employed in the next step without further reaction.

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture is stirred for 20 minutes
  3. filtrationThe ion exchange resin is filtrated off
  4. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-af99f152a82a4cf7882d1903beff57ad
Source dataset
uspto-grants-1990_02
Patent number
US04902811

Reaction notes

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