4-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl Ether → (Z)-4-{[8-(4-tert-Butylphenyl)-5,5-dimethyl-5,6-dihydronaphthalen-2-yl]-trimethylsilanylvinyl}benzyl Alcohol

HRID 1281236Notes

Reaction equation

HRID 1281236 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.BrC1C=C2C(=CC=1)C(C)(C)C[CH:37]=[C:36]2[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[C:51]([CH3:54])([CH3:53])[CH3:52]>>[C:51]([C:46]1[CH:47]=[CH:48][C:49]([C:36]2[C:45]3[CH:50]=[C:49](/[C:27](/[Si:28]([CH3:29])([CH3:30])[CH3:31])=[CH:26]/[C:23]4[CH:22]=[CH:21][C:20]([CH2:19][OH:18])=[CH:25][CH:24]=4)[CH:48]=[CH:47][C:46]=3[C:51]([CH3:53])([CH3:52])[CH2:54][CH:37]=2)=[CH:50][CH:45]=1)([CH3:54])([CH3:53])[CH3:52]

Participants

3

Reactant 2

HCID 102971754-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl EtherHCID 223930916-Bromo-4-(tert-butylphenyl)-1,1-dimethyl-1,2-dihydronaphthalene

Product 1

HCID 23382399(Z)-4-{[8-(4-tert-Butylphenyl)-5,5-dimethyl-5,6-dihydronaphthalen-2-yl]-trimethylsilanylvinyl}benzyl Alcohol

Procedure

Following General Procedure A, 4-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl ether and 6-bromo-4-(tert-butylphenyl)-1,1-dimethyl-1,2-dihydronaphthalene (which can be prepared by the procedure described in Klein, et al., U.S. Pat. No. 5,952,345) were coupled to give the title compound (Compound 29). PNMR (300 MHz, CDCl3): δ0.0 (s, 9 H), 1.48 (s, 6 H), 1.51 (s, 9 H), 2.49 (d, J=4.8 Hz, 2 H), 4.82 (d, J=4.8 Hz, 2 H), 6.13 (t, J=4.8 Hz, 1 H), 7.00 (d, J=1.7 Hz, 1 H), 7.22 (dd, J=1.7, 7.9 Hz, 1 H), 7.30-7.50 (m, 8 H), 7.55 (d, J=8.8 Hz, H).

Workup

  1. customcan be prepared by the procedure

Sources & evidence

ORD record
ord-f46d9f8845034e29ba50280c87baeff0
Source dataset
uspto-grants-2002_09
Patent number
US06452032B1

Reaction notes

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