Water → HCID 67216429, compound

HRID 1969566Notes

Reaction equation

HRID 1969566 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[C@H:14]([CH2:15][CH3:16])[CH2:13][C:12](=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:11]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O.O>C1COCC1>[CH2:15]([C@H:14]1[C@@H:10]([CH2:9][OH:8])[CH2:11][C:12](=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]1)[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 67998516HCID 67998516, compound

Product 1

HCID 67216429HCID 67216429, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-((3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-4-ethylcyclopentylidene)acetate (1.00 g, 3.06 mmol) in THF (20 mL) was added TBAF (1M in THF, 4.59 mL, 4.59 mmol). After 6 h, EtOAc and water were added. The organic layer was separated, concd in vacuo and purified by chromatography on silica gel eluting with EtOAc/heptane to provide ethyl 2-((3R,4S)-3-ethyl-4-(hydroxymethyl)cyclopentylidene)acetate (0.620 g, 95%) as an oil. LC/MS (Table 1, Method a) Rt=1.96, 2.08 min; MS m/z: 213 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. customconcd in vacuo and purified by chromatography on silica gel eluting with EtOAc/heptane

Sources & evidence

ORD record
ord-1729670fcec145358ce6f5710a81cc85
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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