Hydrochloric Acid → HCID 178501146, 화합물

HRID 528698노트

반응식

HRID 528698 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][C:13]([C@H:15]1[CH2:20][CH2:19][C@H:18]([CH2:21][OH:22])[CH2:17][CH2:16]1)=[O:14].C(N(CC)CC)C.Cl>ClCCl>[CH3:11][O:12][C:13]([C@H:15]1[CH2:20][CH2:19][C@H:18]([CH:21]=[O:22])[CH2:17][CH2:16]1)=[O:14]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178501147HCID 178501147, 화합물

생성물 1

HCID 178501146HCID 178501146, 화합물수율 107.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-50 °C

실험 절차

To a solution of dimethylsulfoxide (9.53 g, 122 mmol) in dry dichloromethane (400 ml) was slowly added oxalyl chloride (7.74 g, 61.0 mmol) at −78° C. The cooling bath was removed and the reaction mixture was stirred at −50° C. for 5 min. A solution of trans-4-hydroxymethyl-cyclohexanecarboxylic acid methyl ester (8.75 g, 50.8 mmol) in dichloromethane (108 ml) was added at −65° C. Stirring for 30 minutes was followed by addition of triethylamine (25.7 g, 254 mmol). The cooling bath was removed 15 minutes after completed addition. The reaction mixture was quenched with 1 M aqueous hydrochloric acid solution (152 ml, 152 mmol) at −10° C. The layers were separated. The organic layer was washed with two 250 ml-portions of water and one 100-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as yellow oil (9.3 g, quantitative), which was used in the next step without further purification. MS m/e: 170 (M+)

후처리

  1. customat −78° C
  2. customThe cooling bath was removed
  3. stirringStirring for 30 minutes
  4. customThe cooling bath was removed 15 minutes
  5. additionaddition
  6. customThe layers were separated
  7. washThe organic layer was washed with two 250 ml-portions of water and one 100-ml portion of brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-79435c97d24749389e274427184c3df1
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346824B2

반응 노트

불러오는 중…