Water → HCID 57706946, compound

HRID 1662413Notes

Reaction equation

[CH3:1][C:2]([Si:5]([CH3:30])([CH3:29])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([CH:23](O)[C:24]([CH3:27])([CH3:26])[CH3:25])[CH:9]=1)([CH3:4])[CH3:3].CCN(S(F)(F)[F:37])CC.O>C1(C)C=CC=CC=1>[CH3:3][C:2]([Si:5]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([CH:23]([F:37])[C:24]([CH3:26])([CH3:25])[CH3:27])[CH:9]=1)([CH3:29])[CH3:30])([CH3:1])[CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 66.30B (0.400 g, 0.925 mmol) in toluene (10 mL) at −78° C. was added DAST (0.209 g, 1.29 mmol) dropwise. The reaction was stirred at −78° C. for 30 minutes and then warmed to 23° C. and stirred for an additional 2 hours. Water was added to quench the reaction mixture. The reaction was then extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 66.30C as a colorless oil (0.400 g, 99% yield).

Workup

temperaturewarmed to 23° C.
stirringstirred for an additional 2 hours
customto quench the reaction mixture
extractionThe reaction was then extracted three times with EtOAc
dry with materialAfter drying over anhydrous magnesium sulfate
filtrationfiltering
customthe organic solvent was removed under reduced pressure
customthe product was then purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-0a5c5bd32c1a4513a428344e2e8b800a
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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