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

HRID 496163

반응식

HRID 496163 반응식
[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].S[CH:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.[CH2:20](N(CC)CC)[CH3:21]>COCCOCCOC>[CH2:20]([C:12]([CH2:13][S:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])([CH:17]=[CH:16][CH2:15][CH3:14])[CH:11]=[O:18])[CH3:21]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2회HCID 1382782-MercaptobenzenemethanolHCID 5251295Mercaptobenzyl alcohol

생성물 1

HCID 544309312-Ethyl-2-((2-Hydroxymethylphenyl)thiomethyl)hexenal수율 484.6%

시약·촉매·용매 1

HCID 8150Diglyme용매

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 wasted twice with 10% NaOH, dried over MgSO4 and concentrated in vacto 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. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacto

출처 및 근거

ORD 기록
ord-346d294e4065472690ba939724fcfb29
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943189B2

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