Reaction #81849

ord-f6cec43e01da4b7f9c141f242587d7b6

Reaction equation

CC(C)(C)[Si](OCc1ccc(CCCC=O)cc1)(c1ccccc1)c1ccccc1
172
CC(C)(C)[Si](OCc1ccc(CCCC=O)cc1)(c1ccccc1)c1ccccc1
4-(4-tert-Butyldiphenylsilyloxymethylphenyl) butyraldehyde
[Br][Mg][CH2]CCc1ccccc1
120
[Br][Mg][CH2]CCc1ccccc1
3-Phenyl-1-propylmagnesium bromide
OC(CCCc1ccccc1)CCCc1ccccc1
121
OC(CCCc1ccccc1)CCCc1ccccc1
1,7-Diphenyl-4-heptanol
→
CC(C)(C)[Si](OCc1ccc(CCCC(O)CCCc2ccccc2)cc1)(c1ccccc1)c1ccccc1
alcohol
Yield 122.9%
CC(C)(C)[Si](OCc1ccc(CCCC(O)CCCc2ccccc2)cc1)(c1ccccc1)c1ccccc1
1-(4-tert-Butyldiphenylsilyloxymethylphenyl)-7-phenyl-heptan-4-ol
Yield 122.9%

Reactants

CC(C)(C)[Si](OCc1ccc(CCCC=O)cc1)(c1ccccc1)c1ccccc1
172
CC(C)(C)[Si](OCc1ccc(CCCC=O)cc1)(c1ccccc1)c1ccccc1
4-(4-tert-Butyldiphenylsilyloxymethylphenyl) butyraldehyde
[Br][Mg][CH2]CCc1ccccc1
120
[Br][Mg][CH2]CCc1ccccc1
3-Phenyl-1-propylmagnesium bromide
OC(CCCc1ccccc1)CCCc1ccccc1
121
OC(CCCc1ccccc1)CCCc1ccccc1
1,7-Diphenyl-4-heptanol

Reagents

None

Solvents

C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    WashFlash chromatography (elution with 10% ethyl acetate in hexane)

Procedure

The alcohol 173 was prepared from 2.12 g (5.0 mmol) of 172 and 9.0 mL (9 mmol) of 120 in 50 mL of THF as described for the synthesis of 121 in Example 1. Flash chromatography (elution with 10% ethyl acetate in hexane) gave 3.3 g of the alcohol 173. 1H NMR consistent with the product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05620971uspto-grants-1997_04