Tetrabutylammonium Fluoride → HCID 20775650, compound

HRID 1815996Notes

Reaction equation

HRID 1815996 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[N:12]=[C:13]([CH:16]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][Si](C(C)C)(C(C)C)C(C)C)=[CH:25][CH:24]=2)[CH2:17][C:18]([O:20][CH3:21])=[O:19])[O:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[NH4+].[Cl-]>[CH2:1]([O:8][C:9]([C:11]1[N:12]=[C:13]([CH:16]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[CH2:17][C:18]([O:20][CH3:21])=[O:19])[O:14][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 20775653HCID 20775653, compound

Product 1

HCID 20775650HCID 20775650, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of methyl (±)-3-[4-(benzyloxycarbonyl)-1,3-oxazol-2-yl]-4-[4-(triisopropylsilyloxy)phenyl]butanoate (2.23 g, 4.04 mmole) in dry THF (20 mL) at 0° C. was added a solution of TBAF in THF (1.0 M, 6.06 mL, 6.06 mmole). After 2 hr the mixture was diluted with saturated NH4Cl (10 mL) and extracted with CH2Cl2 (3×15 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel (40% EtOAc/hexanes) to give the title compound (1.4 g. 88%) as an off-white foam: MS (ES) m/e 396 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2 (3×15 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d00dfa2c017d4935b0382b95c00b19ca
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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