Tetrabutylammonium Fluoride → (4E,6E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-2-thienyl]-3-ethylnona-4,6-dien-3-ol

HRID 49334Notes

Reaction equation

HRID 49334 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][C:18](/[C:20](/[CH2:30][CH3:31])=[CH:21]/[CH:22]=[CH:23]/[C:24]([CH2:28][CH3:29])([OH:27])[CH2:25][CH3:26])=[CH:17][CH:16]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[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][C:18](/[C:20](/[CH2:30][CH3:31])=[CH:21]/[CH:22]=[CH:23]/[C:24]([CH2:28][CH3:29])([OH:27])[CH2:25][CH3:26])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 88012109(4E,6E)-7-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}-3-ethylnona-4,6-dien-3-ol

Product 1

HCID 9844826(4E,6E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-2-thienyl]-3-ethylnona-4,6-dien-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

850 mg (1.3 mmol) of (4E,6E)-7-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}-3-ethylnona-4,6-dien-3-ol are dissolved in 20 mL of anhydrous THF. 3.9 mL (3.9 mmol) of 1 M tetrabutylammonium fluoride solution are then added and the medium is stirred for 4 hours. After the usual treatment, the residue is purified by chromatography on silica gel (eluent: 2 heptane/8 ethyl acetate). (4E,6E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-2-thienyl]-3-ethylnona-4,6-dien-3-ol is obtained in the form of a yellow oil (m=340 mg; Y=63%).

Workup

  1. customAfter the usual treatment, the residue is purified by chromatography on silica gel (eluent: 2 heptane/8 ethyl acetate)

Sources & evidence

ORD record
ord-7d5020d3bfe842cc9bb7eddb698b0323
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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