(Diethylamino)sulfur trifluoride → HCID 53975141, compound

HRID 344064Notes

Reaction equation

HRID 344064 reaction equation
O[C:2]1([CH2:19][O:20][C:21](=[O:35])[N:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:3]1.C(N(S(F)(F)[F:42])CC)C>C(Cl)Cl>[F:42][C:2]1([CH2:19][O:20][C:21](=[O:35])[N:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:3]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 53886608HCID 53886608, compound

Product 1

HCID 53975141HCID 53975141, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydroxy-2-(N,N-diphenylcarbamoyloxymethyl)-5-ethoxycarbonylmethyloxy-1,2,3,4-tetrahydronaphthalene (100 mg) in CH2Cl2 (10 ml) was added diethylaminosulfur trifluoride (0.5 ml) at -78° C. After being stirred for 30 minutes, the mixture was washed with sat. NaHCO3 and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 2-fluoro-2-(N,N-diphenylcarbamoyloxymethyl)-5-ethoxycarbonylmethyloxy-1,2,3,4-tetrahydronaphthalene (40 mg).

Workup

  1. washthe mixture was washed with sat. NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9a824b10ac7b4487bfc2c62c79431939
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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