3,4-Dimethyl-3-cyclopenten-1-ol → (1RS,4RS)-4-hydroxy-4-(3-trimethylsilyl-2-propynyl)-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether

HRID 582749Notes

Reaction equation

HRID 582749 reaction equation
CC1CC(O)CC=1C.[Si:9]([O:16][CH:17]1[CH2:21][C:20]([O:29]COC)([CH2:22][C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:18]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>>[Si:9]([O:16][CH:17]1[CH2:21][C:20]([OH:29])([CH2:22][C:23]#[C:24][Si:25]([CH3:26])([CH3:28])[CH3:27])[CH:19]=[CH:18]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 135076013,4-Dimethyl-3-cyclopenten-1-olHCID 56993888(1RS,4RS)-4-methoxymethoxy-4-(3-trimethylsilyl-2-propynyl)-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether

Product 1

HCID 86754280(1RS,4RS)-4-hydroxy-4-(3-trimethylsilyl-2-propynyl)-2-cyclopenten-1-yl (t-butyldimethylsilyl) etherYield 65%

Procedure

From 8.9 g of (1RS,4RS)-4-hydroxy-4-(3-trimethylsilyl-2-propynyl)-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether was obtained by the same procedures as in (3) of the intermediate preparation example 1 (1RS,4RS)-4-methoxymethoxy-4-(3-trimethylsilyl-2-propynyl)-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether in an amount of 6.6 g. Yield 65%

Sources & evidence

ORD record
ord-25cac8c3ae964aff932dbc08f8717973
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

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