Chloroform → HCID 18397096, compound

HRID 376207Notes

Reaction equation

HRID 376207 reaction equation
C(Cl)(Cl)Cl.C([O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([F:23])=[C:18]([C:24]([O:26][C@@H:27]([C:32]([F:35])([F:34])[F:33])[CH2:28][CH2:29][CH2:30][CH3:31])=[O:25])[CH2:17][CH2:16]2)C1C=CC=CC=1.I[Si](C)(C)C>CO>[OH:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([F:23])=[C:18]([C:24]([O:26][C@@H:27]([C:32]([F:33])([F:34])[F:35])[CH2:28][CH2:29][CH2:30][CH3:31])=[O:25])[CH2:17][CH2:16]2

Participants

5

Reactant 3

HCID 6212ChloroformHCID 85247Trimethylsilyl iodideHCID 18397093HCID 18397093, compound

Product 1

HCID 18397096HCID 18397096, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3.1 ml of a chloroform solution of 0.82 g (1.9 mmol) of the (R)1-trifluoromethylpentyl 6-benzyloxy-1-fluoro-3,4-dihydro-2-naphthalenecarboxylate obtained in the third step was dropwise added 134 μl (0.95 mmol) of iodotrimethylsilane, and they were reacted at room temperature for 30 minutes in a nitrogen atmosphere with stirring. Then, 10 ml of methanol was added to terminate the reaction. The reaction mixture was separated by column chromatography, to obtain 0.24 g of (R)1-trifluoromethylpentyl 6-hydroxy-1-fluoro-3,4-dihydro-2-naphthalenecarboxylate (yield: 37%). The 1H-NMR data of this compound are described below.

Workup

  1. customwere reacted at room temperature for 30 minutes in a nitrogen atmosphere
  2. customto terminate
  3. customthe reaction
  4. customThe reaction mixture was separated by column chromatography

Sources & evidence

ORD record
ord-49cc0ffd4f3b47c9b3a3d4e8eea4cef6
Source dataset
uspto-grants-2000_02
Patent number
US06019911

Reaction notes

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