Hydrofluoric Acid → HCID 28561489, compound

HRID 1987831Notes

Reaction equation

HRID 1987831 reaction equation
F.[Si]([O:9][CH2:10][C:11]1[CH:23]=[CH:22][C:14]([O:15][C@H:16]2[CH2:20][CH2:19][O:18][C:17]2=[O:21])=[CH:13][CH:12]=1)(C(C)(C)C)(C)C>CC#N>[OH:9][CH2:10][C:11]1[CH:23]=[CH:22][C:14]([O:15][C@H:16]2[CH2:20][CH2:19][O:18][C:17]2=[O:21])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 14917Hydrofluoric AcidHCID 69069872HCID 69069872, compound

Product 1

HCID 28561489HCID 28561489, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 40% aqueous hydrofluoric acid in CH3CN (10 mL) was added to a 0° C. solution of (S)-3-(4-((tert-butyldimethylsilyloxy)methyl)phenoxy)-dihydrofuran-2(3H)-one in CH3CN (50 mL). The reaction was stirred for 30 minutes and then partitioned between a saturated NaHCO3 solution and diethyl ether. The organics were dried over MgSO4 and concentrated under reduced pressure. The residue was chromatographed to provide the desired product (0.92 g, 72%).

Workup

  1. custompartitioned between a saturated NaHCO3 solution and diethyl ether
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed

Sources & evidence

ORD record
ord-a2954094f3334f2cb5c24d782f08a153
Source dataset
uspto-grants-2009_06
Patent number
US07553842B2

Reaction notes

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