Benzaldehyde → 1-Phenyl-3-(trimethylsilyl)-2-propyn-1-ol

HRID 1654765Notes

Reaction equation

HRID 1654765 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].[CH:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(OCC)C>O1CCCC1.O>[CH3:11][Si:12]([C:15]#[C:16][CH:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:24])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 3283Diethyl EtherHCID 66111TrimethylsilylacetyleneHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 27604161-Phenyl-3-(trimethylsilyl)-2-propyn-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Place lithium hexamethyldisilazane (12 mL of a IM solution in tetrahydrofuran, 12 mmol) under an argon atmosphere and cool to 0° C. Add trimethylsilylacetylene (1.7 mL, 12 mmol) and stir for 1 hour at 0° C. Add benzaldehyde (1.06 g, 10 mmol) in tetrahydrofuran (25 mL). Allow to warm to room temperature and stir for 3 hours. Pour the mixture into ethyl ether and water, separate the organic phase and evaporate the solvent in vacuo. Filter the oil through silica gel (20% ethyl acetate/hexane) and evaporate the solvent in vacuo to yield the title compound.

Workup

  1. customseparate the organic phase
  2. customevaporate the solvent in vacuo
  3. filtrationFilter the oil through silica gel (20% ethyl acetate/hexane)
  4. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-5b258201c8314b418c0c871df7182f89
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

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