Benzaldehyde → (1S)-1-Phenylbut-3-en-1-ol

HRID 728411Notes

Reaction equation

HRID 728411 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH2:10]1[CH2:14]OC[CH2:11]1>C(OCC)C.[Ti]>[C:2]1([C@@H:1]([OH:8])[CH2:14][CH:10]=[CH2:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 21881883Oxolane--water (1/1)

Product 1

HCID 6993460(1S)-1-Phenylbut-3-en-1-olYield 66%

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-74 °C

Procedure

A solution of 1.25 mmol of the titanium compound of Example 2b in 60 ml of diethyl ether is cooled to -74° C., and 0.1 ml (1.0 mmol) of freshly distilled benzaldehyde is added. The slightly yellow, clear solution is stirred for a further 2 hours at -74° C. and 5 ml of a 5N H2O/THF solution are added and the mixture is warmed to RT, stirred for a further hour at this temperature, filtered with suction and concentrated on a rotary evaporator. The crude product (0.80 g of a clear colourless oil) is flash-chromatographed (60 g of silica gel, 35 cm long, cross-section 2 cm, 5 ml/fraction, 0.4 bar, 10:1 toluene/ethanol). 0.098 g of product is obtained. Yield: 66%, ee: 93%.

Workup

  1. temperaturethe mixture is warmed to RT
  2. stirringstirred for a further hour at this temperature
  3. filtrationfiltered with suction
  4. concentrationconcentrated on a rotary evaporator
  5. customThe crude product (0.80 g of a clear colourless oil) is flash-chromatographed (60 g of silica gel, 35 cm long

Sources & evidence

ORD record
ord-7c4fbac6ba2a46c3b2da02bcc8711943
Source dataset
uspto-grants-1991_09
Patent number
US05047557

Reaction notes

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