Tetrabutylammonium Fluoride → HCID 57523002, compound

HRID 1746345Notes

Reaction equation

[Si]([O:8][CH2:9][C@H:10]1[O:12][C@H:11]1[C@H:13]([O:22][CH2:23][O:24][CH3:25])[CH2:14][C:15](=[CH2:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[OH:8][CH2:9][C@H:10]1[O:12][C@H:11]1[C@H:13]([O:22][CH2:23][O:24][CH3:25])[CH2:14][C:15](=[CH2:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 57522091HCID 57522091, compound

Product 1

HCID 57523002HCID 57523002, compoundYield 88%

Procedure

To a well stirred solution of silyl ether 11 (1.1 g, 2.94 mmol) was added 1 M solution of tetrabutylammonium fluoride (6.2 mL, 5.87 mmol) at 0° C. The reaction mixture was stirred at this temperature for 2 h after which the solvent was removed under reduced pressure and the residue was subjected to column chromatography with petroleum ether/ethyl acetate (5:5 v/v) to afford free alcohol 12 oily liquid.

Workup

customwas removed under reduced pressure

Sources & evidence

ORD record: ord-03b0d5493bd2469580186c48a1ccf1f6
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150498B2

Reaction notes

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