Chloroform → HCID 18397091, compound

HRID 376206Notes

Reaction equation

HRID 376206 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][C@@H:26]([C:35]([F:38])([F:37])[F:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH3:34])=[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:35]([F:36])([F:37])[F:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH3:34])=[O:24])[CH2:17][CH2:16]2

Participants

5

Reactant 3

HCID 6212ChloroformHCID 85247Trimethylsilyl iodideHCID 18397089HCID 18397089, compound

Product 1

HCID 18397091HCID 18397091, compoundYield 414.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 ml of a chloroform solution of 0.19 g (0.4 mmol) of the (R)1-trifluoromethyl-6-ethoxyhexyl 6-benzyloxy-3,4-dihydro-2-naphthalenecarboxylate obtained in the first step was added 0.1 ml (0.4 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, 8 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 0.64 g of (R)1-trifluoromethyl-6-ethoxyhexyl 6-hydroxy-3,4-dihydro-2-naphthalenecarboxylate as a crude product. The 1H-NMR data of this compound are described below. 1H-NMR (CDCl3), δ (ppm)

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-f02ffdd1b851419385eb5f51eda019e2
Source dataset
uspto-grants-2000_02
Patent number
US06019911

Reaction notes

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