Acetic Acid → HCID 14718886, compound

HRID 1085713Notes

Reaction equation

C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][C:12]([C:15]1[N:20]=[CH:19][C:18]([C:21](=[C:39]([CH3:41])[CH3:40])[C:22]([O:24][CH2:25][C:26]2[C:31]([F:32])=[C:30]([F:33])[C:29]([CH2:34][O:35][CH3:36])=[C:28]([F:37])[C:27]=2[F:38])=[O:23])=[CH:17][N:16]=1)([CH3:14])[CH3:13].C(O)(=O)C>O1CCCC1>[CH3:14][C:12]([C:15]1[N:16]=[CH:17][C:18]([CH:21]([C:39]([CH3:41])=[CH2:40])[C:22]([O:24][CH2:25][C:26]2[C:31]([F:32])=[C:30]([F:33])[C:29]([CH2:34][O:35][CH3:36])=[C:28]([F:37])[C:27]=2[F:38])=[O:23])=[CH:19][N:20]=1)([CH3:11])[CH3:13]

Participants

Conditions

Temperature: -78 °C

Procedure

A 1 molar solution of lithium hexamethyldisilazide (0.125 cm3) in dry tetrahydrofuran was added to a stirred solution of 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl 2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3-methylbut-2-enoate (0.05 g) in dry tetrahydrofuran (1 cm3) whilst the reaction temperature was maintained at -78° C. After 30 minutes, acetic acid (0.01 g) was added in one portion, and the stirred reaction mixture was allowed to warm to the ambient temperature, and quenched with water. Extraction into ethyl acetate, and concentration by removal of the solvent under reduced pressure gave 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (RS)-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl)-3-methylbut-3-enoate (0.05 g).

Workup

customthe stirred reaction mixture
temperatureto warm to the ambient temperature
customquenched with water
extractionExtraction
concentrationinto ethyl acetate, and concentration
customby removal of the solvent under reduced pressure

Sources & evidence

ORD record: ord-2953d1e4ebe5411da9b99462dca04cc4
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05010200

Reaction notes

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