CID 406 → HCID 67998516, compound

HRID 1969565Notes

Reaction equation

HRID 1969565 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.P(=O)([O-])[O-].[Si:21]([O:28][CH2:29][C@@H:30]1[C@H:34]([CH2:35][CH3:36])[CH2:33][C:32](=O)[CH2:31]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Si:21]([O:28][CH2:29][C@@H:30]1[C@H:34]([CH2:35][CH3:36])[CH2:33][C:32](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:31]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23]

Participants

8

Reactant 5

HCID 406CID 406HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 58557220HCID 58557220, compound

Product 1

HCID 67998516HCID 67998516, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of NaH (60% dispersion in mineral oil, 0.608 g, 15.2 mmol) in THF (50 mL) was added ethyl 2-(diethoxyphosphoryl)acetate (3.25 mL, 16.2 mmol). After about 30 min, the phosphonate solution was added to a flask charged with (3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-4-ethylcyclopentanone (2.6 g, 10.14 mmol). After about 20 h, EtOAc (20 mL) and saturated aqueous NH4Cl (20 mL) were added. The organic layer was removed concd in vacuo and purified by chromatography on silica gel eluting with EtOAc/heptane (20-60%) to provide ethyl 2-((3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-4-ethylcyclopentylidene)acetate (3.3 g, 100%) as an oil. LC/MS (Table 1, Method a) Rt=3.91, 3.96 min; MS m/z: 327 (M+H)+.

Workup

  1. waitAfter about 20 h
  2. customThe organic layer was removed concd in vacuo
  3. custompurified by chromatography on silica gel eluting with EtOAc/heptane (20-60%)

Sources & evidence

ORD record
ord-a1e4a76c6b2e493ca185d9ebd779d780
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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