Sodium Iodide → (S)-1-iodo-3-phenyl-3-propanol

HRID 247814

反応式

HRID 247814 の反応式
Cl[CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[I-:12].[Na+]>C(N(CC)CC)C.C(C(C)=O)C>[I:12][CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]

参加物

5

反応物 2

HCID 5238Sodium IodideHCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanol

生成物 1

HCID 14476876(S)-1-iodo-3-phenyl-3-propanol収率 74.9%

試薬・触媒・溶媒 2

HCID 8471Triethylamine触媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

Commerically available (S)-3-chloro-1-phenyl-1-propanol (6 g) was heated with excess sodium iodide (4 equiv., 18 g) and a few drops of triethylamine in 30 mL of methyl ethyl ketone at 100° C. for 20 hours. A sample was taken and monitored by NMR to determine the extent of conversion. The solvent was removed in vacuo and the residue was taken up in dichloromethane and filtered to remove the salts and the iodoalcohol was purified by flash chromatography to yield 6.9 g of product.

後処理

  1. customThe solvent was removed in vacuo
  2. filtrationfiltered
  3. customto remove the salts
  4. customthe iodoalcohol was purified by flash chromatography

出典と根拠

ORDレコード
ord-278df93dbd6b44d1b998b0215d6a2550
出典データセット
uspto-grants-1993_05
特許番号
US05208222

関連ノート

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