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

HRID 1531343Notes

Reaction equation

HRID 1531343 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=O)=[CH:11][CH:10]=1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>>[Si:19]([O:15][CH2:13][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][OH:7])=[CH:18][CH:17]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

4

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81325Methyl 4-(hydroxymethyl)benzoateHCID 21226445Aluminium lithium hydride2×

Product 1

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

Procedure

(Formula II, R1=tert-butyldimethylsilyloxymethylphenyl, R2=4-tert-butyldimethylsilyloxymethylbenzyl). 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) δ 0.08 (32H, s), 0391 (18H, s), 4.22 (1H, d, J 2 Hz), 4.68 (5H, br s), 4.90 (2H, a), 7.1-7.6 (8H, m); MS (CH4) 483 (M+−CH3, 52%), 133 100%).

Sources & evidence

ORD record
ord-ee0d8a19d90b40398092a5363ba599dd
Source dataset
uspto-grants-2001_03
Patent number
US06197905B1

Reaction notes

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