Benzaldehyde → 85551-57-1

HRID 728413Notes

Reaction equation

HRID 728413 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 702233885551-57-1Yield 66%

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-74 °C

Procedure

A solution of 2.25 mmol of the titanium compound of Example 1b in 120 ml of diethyl ether is cooled to -74° C. and 0.2 ml (2.0 mmol) of freshly distilled benzaldehyde is added. The beige suspension is stirred for a further 2 hours at -74° C. and 5 ml of a 5N H2O/THF solution are added. The beige suspension is warmed to RT, stirred for a further hour at this temperature, filtered with suction and concentrated on a rotary evaporator. The crude product (1.53 g of yellow-brown oil) is flash-chromatographed twice (80 g of silica gel, 25 cm long, cross-section 2 cm, 10 ml/fraction, 0.5 bar, 20:1 toluene/ethanol); (50 g of silica gel, 25 cm long, cross-section 2 cm, 15 ml/fraction, 0.5 bar, 15:1 toluene/ethanol). 0.2 g of product are obtained. Yield: 66%, ee: 82%.

Workup

  1. temperatureThe beige suspension 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 (1.53 g of yellow-brown oil) is flash-chromatographed twice (80 g of silica gel, 25 cm long

Sources & evidence

ORD record
ord-5473e24989564253a369718c6567d8a1
Source dataset
uspto-grants-1991_09
Patent number
US05047557

Reaction notes

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