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

HRID 1654761Notes

Reaction equation

HRID 1654761 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-olYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Place lithium hexamethyldisilazane (20 mL of a 1M solution in tetrahydrofuran, 20 mmol) under an argon atmosphere and cool to 0° C. Add, by dropwise addition, trimethylsilylacetylene (2.83 mL, 20 mmol) and stir for 1 hour at 0° C. Add benzaldehyde (2.03 mL, 20 mmol) in tetrahydrofuran (10 mL). Allow to warm to room temperature and stir for 1 hour. 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 4.09 g of the title compound.

Workup

  1. temperatureAllow to warm to room temperature
  2. stirringstir for 1 hour
  3. customseparate the organic phase
  4. customevaporate the solvent in vacuo
  5. filtrationFilter the oil through silica gel (20% ethyl acetate/hexane)
  6. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-499b7b88eb184209b78aee6d29f2b4f9
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

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