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

HRID 1770308Notes

Reaction equation

HRID 1770308 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:34]=[CH:33][C:13]([CH2:14][O:15]C(C2C=CC(CO[Si](C(C)(C)C)(C)C)=CC=2)=C)=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](OCC(OC(C1C=CC=C(CO[Si](C(C)(C)C)(C)C)C=1)=C)C1C=CC=CC=1)(C(C)(C)C)(C)C.C(OC(C1C=CC=C(COC(=O)C)C=1)=C)C1C=CC=CC=1.OCC1C=CC(C(OC)=O)=CC=1.[Si](Cl)(C(C)(C)C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[Si:1]([O:8][CH2:9][C:10]1[CH:34]=[CH:33][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 6

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81325Methyl 4-(hydroxymethyl)benzoateHCID 21224724alpha-[(tert-Butyldimethylsilyloxymethyl)-benzyloxy][3-(tert-butyldimethylsilyloxymethyl)styrene]HCID 21226445Aluminium lithium hydrideHCID 21253611alpha-Benzyloxy[3-(acetoxymethyl)styrene]HCID 21253626alpha-[4-(tert-Butyldimethylsilyloxymethyl)-benzyloxy][4-(tert-butyldimethylsilyloxymethyl)styrene]

Product 1

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

Procedure

α-[4-(tert-Butyldimethylsilyloxymethyl)-benzyloxy][4-(tert-butyldimethylsilyloxymethyl)styrene] and α-[(tert-Butyldimethylsilyloxymethyl)-benzyloxy][3-(tert-butyldimethylsilyloxymethyl)styrene]. (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 (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-7a56c8c5f16e4169a62294381859eada
Source dataset
uspto-grants-1995_01
Patent number
US05385996

Reaction notes

Loading…