6-Bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene → (Z)-5-[2-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-(trimethylsilyl)vinyl]thiophene-2-ylmethyl Alcohol

HRID 1281233Notes

Reaction equation

HRID 1281233 reaction equation
[Si]([O:18][CH2:19][C:20]1[S:21][C:22]([C:25]#[C:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.Br[C:32]1[C:41]([CH3:42])=[CH:40][C:39]2[C:38]([CH3:44])([CH3:43])[CH2:37][CH2:36][C:35]([CH3:46])([CH3:45])[C:34]=2[CH:33]=1>>[CH3:42][C:41]1[C:32](/[C:26](/[Si:27]([CH3:28])([CH3:29])[CH3:30])=[CH:25]/[C:22]2[S:21][C:20]([CH2:19][OH:18])=[CH:24][CH:23]=2)=[CH:33][C:34]2[C:35]([CH3:46])([CH3:45])[CH2:36][CH2:37][C:38]([CH3:44])([CH3:43])[C:39]=2[CH:40]=1

Participants

3

Reactant 2

HCID 100393466-Bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthaleneHCID 223930945-[(Trimethylsilyl)ethynyl]thiophen-2-ylmethyl Tert-butyldiphenylsilyl Ether2×

Product 1

HCID 23382405(Z)-5-[2-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-(trimethylsilyl)vinyl]thiophene-2-ylmethyl Alcohol

Procedure

Following General Procedure A, 5-[(trimethylsilyl)ethynyl]thiophen-2-ylmethyl tert-butyldiphenylsilyl Ether (Compound 13, 0.75 g, 1.8 mmol) and 2-bromo-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene (0.45 g, 1.67 mmol) were coupled to give the title compound.

Sources & evidence

ORD record
ord-3977f249f265455a853e2706509136b7
Source dataset
uspto-grants-2002_09
Patent number
US06452032B1

Reaction notes

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