Tetrabutylammonium Fluoride → HCID 86746995, compound

HRID 1588440Notes

Reaction equation

HRID 1588440 reaction equation
[O:1]([CH:9]([C:36]([F:41])([F:40])[CH2:37][CH2:38][CH3:39])[CH2:10][CH2:11][CH2:12][C@H:13]1[C@H:17]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH2:16][C@H:15]([OH:25])[C@@H:14]1[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:41][C:36]([F:40])([CH2:37][CH2:38][CH3:39])[CH:9]([OH:1])[CH2:10][CH2:11][CH2:12][C@H:13]1[C@H:17]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH2:16][C@H:15]([OH:25])[C@@H:14]1[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131717999HCID 131717999, compound

Product 1

HCID 86746995HCID 86746995, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl (Z)-7-[(1R)-(2R,3R,5S)-2-{4(RS)-t-butyldimethylsiloxy-5,5-difluorooctyl}-5-hydroxy-3-tetrahydropyranyloxycyclopentyl]hept-5-enoate (17) (1.90 g) in tetrahydrofuran was added tetrabutylammonium fluoride in tetrahydrofuran (1.0M, 15.7 ml). The resultant mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure and the obtained residue was subjected to silicagel column chromatography to give the titled compound (18).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-553d2eba69104138b3bfca5a49233477
Source dataset
uspto-grants-1993_06
Patent number
US05221799

Reaction notes

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