6-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene → (Z)-4-[2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-(trimethylsilyl)vinyl]benzyl Alcohol

HRID 1281228Notes

Reaction equation

HRID 1281228 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:42]=[CH:41][C:40]2[C:39]([CH3:44])([CH3:43])[CH2:38][CH2:37][C:36]([CH3:46])([CH3:45])[C:35]=2[CH:34]=1>>[CH3:43][C:39]1([CH3:44])[CH2:38][CH2:37][C:36]([CH3:46])([CH3:45])[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 2266856-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthaleneHCID 102971754-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl Ether2×

Product 1

HCID 9821901(Z)-4-[2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-(trimethylsilyl)vinyl]benzyl Alcohol

Procedure

Following General Procedure A, 4-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl ether (Compound 2, 0.89 g, 2.0 mmol) and 2-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (0.60 g, 2.25 mmol) were coupled to give the title compound. 2-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene can be prepared in accordance with the procedure set forth in J. Med. Chem. 34:2930-41 (1994). The pentamethyl derivative thereof can be prepared in accordance with the same procedure.

Sources & evidence

ORD record
ord-04ec3a9bf4ea41ff818143643d1c49fa
Source dataset
uspto-grants-2002_09
Patent number
US06452032B1

Reaction notes

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