HCID 69958623, compound → HCID 69960966, compound

HRID 850198Notes

Reaction equation

HRID 850198 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[C:22](/[C:27](/[CH3:50])=[CH:28]\[CH2:29][O:30]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:21]=1[CH3:51])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C>[Si:1]([O:18][CH2:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[C:22](/[C:27](/[CH3:50])=[CH:28]\[CH2:29][OH:30])[C:21]=1[CH3:51])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 69958623HCID 69958623, compound

Product 1

HCID 69960966HCID 69960966, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-tert-butyldiphenylsilyloxymethyl-2,6-dimethyl-3-((Z)-1-methyl-3-trityloxy-1-propenyl)benzene (500 mg) in acetic acid (5 ml) was heated at 60° C. for 10 hours. The cooled reaction mixture was concentrated in vacuo and ethyl acetate was added thereto. The mixture was washed with aqueous sodium bicarbonate solution, water and brine, dried over magnesium sulfate and evaporated in vacua. The residue was purified by flash silica gel chromatography eluted with n-hexane-ethyl acetate to give 1-tert-butyldiphenylsilyloxymethyl-2,6-dimethyl-3-((Z)-3-hydroxy-1-methyl-1-propenyl)benzene (92 mg) as colorless oil.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo and ethyl acetate
  3. additionwas added
  4. washThe mixture was washed with aqueous sodium bicarbonate solution, water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacua
  7. customThe residue was purified by flash silica gel chromatography
  8. washeluted with n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-09dcd340fdba4062892416e645251b2a
Source dataset
uspto-grants-2000_01
Patent number
US06015818

Reaction notes

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