Tetrabutylammonium Fluoride → Diethyl [1-hydroxy-(E,E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]phosphonate

HRID 488168Notes

Reaction equation

[O:1]([CH:9]([P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])[CH2:10]/[CH:11]=[C:12](\[CH3:24])/[CH2:13][CH2:14]/[CH:15]=[C:16](\[CH3:23])/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:1][CH:9]([P:25](=[O:32])([O:26][CH2:27][CH3:28])[O:29][CH2:30][CH3:31])[CH2:10]/[CH:11]=[C:12](\[CH3:24])/[CH2:13][CH2:14]/[CH:15]=[C:16](\[CH3:23])/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the diethyl [1-(t-butyldimethylsiloxy)-(E,E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]phosphonate (55 mg, 0.113 mmol) in THF (1 ml), under argon, at 0° C. was added tetrabutylammonium fluride (0.113 ml of a 1.0M solution in THF, 0.113 mmol), and the mixture stirred at 0° C. for 1 hr. The solvent was evaporated in vacuo and the residue chromatographed on silica gel eluted with ethylacetate:hexanes, (3:1, v:v) to afford the title compound (37 m,g 88%) as an oil.

Workup

customThe solvent was evaporated in vacuo
customthe residue chromatographed on silica gel
washeluted with ethylacetate

Sources & evidence

ORD record: ord-67fc2bfab3e140a8a6f6ef08f6055272
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05298655

Reaction notes

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