3-(t-Butyldimethylsilyloxy)benzaldehyde → 1-[3-(tert-Butyldimethylsilanyloxy)phenyl]propan-1-ol

HRID 644568Notes

Reaction equation

HRID 644568 reaction equation
[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])([CH3:4])([CH3:3])[CH3:2].[CH2:17]([Mg]Br)[CH3:18]>C(OCC)C>[Si:5]([O:6][C:7]1[CH:8]=[C:9]([CH:10]([OH:11])[CH2:17][CH3:18])[CH:12]=[CH:13][CH:14]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 112071113-(t-Butyldimethylsilyloxy)benzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 685795511-[3-(tert-Butyldimethylsilanyloxy)phenyl]propan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

50 g (0.21 mol) of 3-(tert-butyldimethyl-silanyloxy)benzaldehyde are dissolved in 500 ml of ethyl ether and the mixture is cooled to 0° C. 80 ml (0.24 mol) of a 3.0 M solution of ethylmagnesium bromide are added slowly, and the mixture is stirred for 5 hours. After the usual treatment, the residue obtained is purified by chromatography on a silica column (eluent ethyl acetate 20/hexane 80). A colorless oil is obtained (m=45.8 g; Y=82%).

Workup

  1. customAfter the usual treatment, the residue obtained
  2. customis purified by chromatography on a silica column (eluent ethyl acetate 20/hexane 80)
  3. customA colorless oil is obtained (m=45.8 g; Y=82%)

Sources & evidence

ORD record
ord-4b4a01cb649a4491bf392461ba2c5fac
Source dataset
uspto-grants-2010_04
Patent number
US07700657B2

Reaction notes

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