tert-Butyldimethylsilyl chloride → Benzenemethanol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

HRID 1584520Notes

Reaction equation

HRID 1584520 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=O)=[CH:5][CH:4]=1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[Si:13]([O:9][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[CH:12][CH:11]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

4

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81325Methyl 4-(hydroxymethyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10800836Benzenemethanol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

Procedure

Methyl 4-(hydroxymethyl)benzoate was treated with tert-butyldimethylsilyl chloride using the general procedure described in Journal of the American Chemical Society, 1972, 94, 6190. The resulting product was reduced with lithium aluminium hydride to afford 4-(tert-butyldimethylsilyloxymethyl)benzyl alcohol. This alcohol was converted into the required compound using Method C. 1H NMR (CCl4) δ0.08 (12H, s), 0.91 (18H, s), 4.22 (1H, d, J 2 Hz), 4.68 (5H, br s), 4.90 (2H, s), 7.1-7.6 (8H, m); MS (CH4) 483 (M+ -CH3, 52%), 133 100% ).

Sources & evidence

ORD record
ord-05b319553c1a443e958cda8e8af27259
Source dataset
uspto-grants-1999_08
Patent number
US05932675

Reaction notes

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