Chloroform → HCID 18397098, compound

HRID 376205Notes

Reaction equation

HRID 376205 reaction equation
C(Cl)(Cl)Cl.C([O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C:23]([O:25][CH:26]([C:31]([F:34])([F:33])[F:32])[CH2:27][CH2:28][CH2:29][CH3:30])=[O:24])[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)[CH:19]=[C:18]([C:23]([O:25][C@@H:26]([C:31]([F:32])([F:33])[F:34])[CH2:27][CH2:28][CH2:29][CH3:30])=[O:24])[CH2:17][CH2:16]2

Participants

5

Reactant 3

HCID 6212ChloroformHCID 85247Trimethylsilyl iodideHCID 193608811-Trifluoromethylpentyl 6-benzyloxy-3,4-dihydro-2-naphthalenecarboxylate

Product 1

HCID 18397098HCID 18397098, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 ml of a chloroform solution of 0.23 g (0.5 mmol) of the (R) 1-trifluoromethylpentyl 6-benzyloxy-3,4-dihydro-2-naphthalenecarboxylate obtained in the third step was added 0.1 ml (0.7 mmol) of iodotrimethylsilane in a nitrogen atmosphere with stirring, and the mixture was reacted at room temperature for two and a half hours with stirring. Then, 10 ml of methanol was added, and the mixture was rapidly concentrated at room temperature under reduced pressure. The concentrate was separated by column chromatography, to obtain 0.11 g of (R)1-trifluoromethylpentyl 6-hydroxy-3,4-dihydro-2-naphthalenecarboxylate as a white solid (yield: 61%). The 1H-NMR data of this compound are described below.

Workup

  1. customthe mixture was reacted at room temperature for two and a half hours
  2. stirringwith stirring
  3. concentrationthe mixture was rapidly concentrated at room temperature under reduced pressure
  4. customThe concentrate was separated by column chromatography

Sources & evidence

ORD record
ord-67d193232ac94bc3afba94094bfaf0bd
Source dataset
uspto-grants-2000_02
Patent number
US06019911

Reaction notes

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