Hydrochloric Acid → 2-Ethyl-2-((2-Hydroxymethylphenyl)thiomethyl)hexenal

HRID 478886

반응식

HRID 478886 반응식
[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[CH2:10]([C:12]([CH2:19]OS(C)(=O)=O)([CH2:15][CH2:16][CH2:17][CH3:18])[CH:13]=[O:14])[CH3:11].SC(O)C1C=CC=CC=1.Cl>C(N(CC)CC)C.COCCOCCOC>[CH2:10]([C:12]([CH2:19][S:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])([CH:15]=[CH:16][CH2:17][CH3:18])[CH:13]=[O:14])[CH3:11]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1382782-MercaptobenzenemethanolHCID 5251295Mercaptobenzyl alcoholHCID 115722172-Ethyl-2-(mesyloxymethyl)hexanal

생성물 1

HCID 544309312-Ethyl-2-((2-Hydroxymethylphenyl)thiomethyl)hexenal수율 107.8%

시약·촉매·용매 2

HCID 8150Diglyme용매HCID 8471Triethylamine용매2회

실험 절차

A mixture of 5.0 g (0.036 mole) of 2-mercaptobenzyl alcohol, 6.4 g (0.032 mole) of 1, 3.6 g (0.036 mole) of triethylamine and 25 mL of 2-methoxyethyl ether was held at reflux for 7 h. Additional 1.1 g of mercaptobenzyl alcohol and 0.72 g of triethylamine was added to the reaction mixture and the mixture was held at reflux for additional 16 h. The reaction mixture was cooled and poured into 6N HCl and extracted with methylene chloride. The methylene chloride extract was washed twice with 10% NaOH, dried over MgSO4 and concentrated in vacuo to give 9.6 g of residue. Purification by HPLC (20% EtOAc-hexane) gave 3.7 g (41%) of 16 as an oil.

후처리

  1. temperatureat reflux for 7 h
  2. temperatureat reflux for additional 16 h
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. washwas washed twice with 10% NaOH
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f7dd7cd9bbc04888b4817b8ee5124c3b
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642268B2

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