Bicarbonate Ion → 1-But-3-enyl-4-cyclohexyl-benzene

HRID 237883

Reaction equation

HRID 237883 reaction equation
[CH:1]1([C:7]2[CH:28]=[CH:27][C:10]([CH2:11]OP(C3C=CC=CC=3)(C3C=CC=CC=3)=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:29]([Si](C)(C)C)[CH:30]=[CH2:31].C[Si](OS(C(F)(F)F)(=O)=O)(C)C.C(=O)(O)[O-]>COC(OC)C>[CH2:11]([C:10]1[CH:9]=[CH:8][C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[CH:28][CH:27]=1)[CH2:31][CH:30]=[CH2:29]

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 65367Trimethylsilyl triflateHCID 69808AllyltrimethylsilaneHCID 68529340Diphenyl-phosphinic acid 4-cyclohexyl-benzyl ester

Product 1

HCID 866402421-But-3-enyl-4-cyclohexyl-benzeneYield 82%

Reagents, catalysts & solvents 1

HCID 107951,1-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of diphenyl-phosphinic acid 4-cyclohexyl-benzyl ester (1 g, 2.56 mmol) and 1.22 ml (7.69 mmol) of allyltrimethylsilane in 12 ml of dry dimethoxy-ethane at 0° C. was added 0.46 ml of trimethylsilyltriflate. The mixture was stirred at 0° C. for 1 h, poured into saturated bicarbonate, extracted with ethyl acetate, washed with water, dried (sodium sulfate) filtered and concentrated. The material was purified by chromatography on silica gel, eluting with ethyl acetate/heptane to provide 0.45 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material was purified by chromatography on silica gel
  7. washeluting with ethyl acetate/heptane

Sources & evidence

ORD record
ord-4eae31e673ae496d881f5e6693c56fa0
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Linked notes

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