4-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl Ether → 4-[(Z)-(5,5-Dimethyl-8-p-tolyl-5,6-dihydronaphthalen-2-yl)trimethylsilanylvinyl]-benzyl Alcohol

HRID 1281235Notes

Reaction equation

HRID 1281235 reaction equation
[Si]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[CH:22][CH:21]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.Br[C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[C:39]([CH3:44])([CH3:43])[CH2:38][CH:37]=[C:36]2[C:45]1[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=1>>[CH3:43][C:39]1([CH3:44])[CH2:38][CH:37]=[C:36]([C:45]2[CH:46]=[CH:47][C:48]([CH3:51])=[CH:49][CH:50]=2)[C:35]2[CH:34]=[C:33](/[C:27](/[Si:28]([CH3:29])([CH3:30])[CH3:31])=[CH:26]/[C:23]3[CH:22]=[CH:21][C:20]([CH2:19][OH:18])=[CH:25][CH:24]=3)[CH:42]=[CH:41][C:40]1=2

Participants

3

Reactant 2

HCID 102971754-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl EtherHCID 106876226-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydronaphthalene

Product 1

HCID 233824034-[(Z)-(5,5-Dimethyl-8-p-tolyl-5,6-dihydronaphthalen-2-yl)trimethylsilanylvinyl]-benzyl Alcohol

Procedure

Following General Procedure A, 4-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl ether and 6-bromo-1,1 -dimethyl-4-p-tolyl-1,2-dihydronaphthalene (prepared as described in Klein, et al., U.S. Pat. No. 5,952,345) were coupled to give the title compound (Compound 23). PNMR (300 MHz, CDCl3): δ0.13 (s, 9 H), 1.47 (s, 6 H), 2.48 (d, J=4.4 Hz, 2 H), 2.54 (s, 3 H), 4.82 (d, J=6.1 Hz, 2 H), 6.10 (t, J=4.4 Hz, 1 H), 7.00 (d, J=2.2 Hz, 1 H), 7.18 (dd, J=2.2, 7.9 Hz, 1 H), 7.30-7.45 (m, 10 H).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-462f39a9e10942559f28453d1a31fd9f
Source dataset
uspto-grants-2002_09
Patent number
US06452032B1

Reaction notes

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