Acetic Acid → HCID 10689764, compound

HRID 2394507Notes

Reaction equation

[CH3:1]C(C)([O-])C.[K+].[N+](=CP(=O)(OC)OC)=[N-].[CH3:16][O:17][C:18]1([O:40][CH3:41])[CH2:23][CH2:22][C:21]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[CH:27]=2)([CH:24]=O)[CH2:20][CH2:19]1.C(O)(=O)C>O1CCCC1>[CH3:41][O:40][C:18]1([O:17][CH3:16])[CH2:19][CH2:20][C:21]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH:35]3[CH2:36][CH2:37][CH2:38][CH2:39]3)[CH:27]=2)([C:24]#[CH:1])[CH2:22][CH2:23]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of potassium t-butoxide (0.155 g, 1.38 mmol) in dry tetrahydrofuran (5 mL) under an argon atmosphere at -78° C. was added a solution of dimethyl (diazomethyl)phosphonate (ca. 88% pure, 0.24 g, 1.38 mmol). After 0.25 h, a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-formylcyclohexan-1-one dimethyl ketal (0.42 g, 1.15 mmol) in dry tetrahydrofuran (5 mL) was added dropwise and the mixture was allowed to stir at -78° C. under an argon atmosphere for 5 h. Aqueous acetic acid was added, the mixture was concentrated, partitioned between methylene chloride and water and extracted twice. The organic extract was dried (magnesium sulfate) and evaporated. Purification by flash chromatography, eluting with 3:1 hexanes/ethyl acetate, provided an oil (0.13 g, 32%).

Workup

concentrationthe mixture was concentrated
custompartitioned between methylene chloride and water
extractionextracted twice
extractionThe organic extract
dry with materialwas dried (magnesium sulfate)
customevaporated
customPurification by flash chromatography
washeluting with 3:1 hexanes/ethyl acetate

Sources & evidence

ORD record: ord-4cf11aa4acd34522a2f91d9140050d64
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05811455

Reaction notes

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