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

HRID 49362Notes

Reaction equation

HRID 49362 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:32]=[CH:33][C:34]=1[CH2:35][O:36][Si](C(C)(C)C)(C)C)[O:13][CH2:14][C:15]1[S:19][CH:18]=[C:17](/[C:20](/[CH2:30][CH3:31])=[CH:21]/[CH2:22][CH2:23][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:32]=[CH:33][C:34]=1[CH2:35][OH:36])[O:13][CH2:14][C:15]1[S:19][CH:18]=[C:17](/[C:20](/[CH2:30][CH3:31])=[CH:21]/[CH2:22][CH2:23][C:24]([CH2:28][CH3:29])([OH:27])[CH2:25][CH3:26])[CH:16]=1

Participants

3

Reactant 1

HCID 69825106(E)-7-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}-3-ethylnon-6-en-3-ol

Product 1

HCID 69825176(E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-3-thienyl]-3-ethylnon-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 1 g (1.5 mmol) of (E)-7-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-3-thienyl}-3-ethylnon-6-en-3-ol with 3.7 mL (3.7 mmol) of 1.0 M tetrabutylammonium bromide, the desired product is obtained in the form of white crystals (m.p.=73-74° C.; m=480 mg; Y=74%).

Sources & evidence

ORD record
ord-83c0006c1ab04db4a6b3098f6195c325
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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