(E)-7-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}-3-ethyl-4,4-dimethylnon-6-en-3-ol → (E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-3-thienyl]-3-ethyl-4,4-dimethylnon-6-en-3-ol

HRID 49361Notes

Reaction equation

HRID 49361 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:34]=[CH:35][C:36]=1[CH2:37][O:38][Si](C(C)(C)C)(C)C)[O:13][CH2:14][C:15]1[S:19][CH:18]=[C:17](/[C:20](/[CH2:32][CH3:33])=[CH:21]/[CH2:22][C:23]([CH3:31])([CH3:30])[C:24]([CH2:28][CH3:29])([OH:27])[CH2:25][CH3:26])[CH:16]=1)(C(C)(C)C)(C)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:34]=[CH:35][C:36]=1[CH2:37][OH:38])[O:13][CH2:14][C:15]1[S:19][CH:18]=[C:17](/[C:20](/[CH2:32][CH3:33])=[CH:21]/[CH2:22][C:23]([CH3:31])([CH3:30])[C:24]([CH2:28][CH3:29])([OH:27])[CH2:25][CH3:26])[CH:16]=1

Participants

3

Reactant 1

HCID 69824849(E)-7-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}-3-ethyl-4,4-dimethylnon-6-en-3-ol

Product 1

HCID 69825263(E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-3-thienyl]-3-ethyl-4,4-dimethylnon-6-en-3-ol

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

In a manner similar to that of Example 6(l), by reaction of 310 mg (0.46 mmol) of (E)-7-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}-3-ethyl-4,4-dimethylnon-6-en-3-ol with 1.1 mL (1.1 mmol) of 1.0 M tetrabutylammonium bromide, the desired product is obtained in the form of a colourless oil (m=200 mg; Y=98%).

Sources & evidence

ORD record
ord-1fc01db0edff4e939516c2769e8aaaa0
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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