Benzene → HCID 14514901, 화합물

HRID 486948노트

반응식

HRID 486948 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10](O)[CH2:11][CH2:12][CH3:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[SH:15][CH2:16][C:17]([OH:19])=[O:18].C1C=CC=CC=1>CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.CCOCC>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([S:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:11][CH2:12][CH3:13])=[CH:9][C:4]=2[O:3][CH2:2]1

참가 물질

6

반응물 3

HCID 241BenzeneHCID 1133Thioglycolic AcidHCID 10375365HCID 10375365, 화합물

생성물 1

HCID 14514901HCID 14514901, 화합물수율 89.3%

시약·촉매·용매 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-촉매HCID 3283Diethyl Ether용매

실험 절차

A mixture comprising 103 g of 1-(1,3-benzodioxol-5-yl)-1-butanol, 73.3 g of mercaptoacetic acid, 0.1 g of D-10-camphorsulfonic acid and 500 ml of benzene was heated under reflux for 2 hours, followed by the addition of 2000 ml of ether. The obtained mixture was washed with water and extracted with 750 ml and then 100 ml of 1 N sodium hydroxide successively. The extracts were combined, washed with ether and chloroform successively, acidified with concentrated hydrochloric acid and extracted with ethyl acetate (800 ml and 400 ml). The extracts were combined, washed with water, dried over magnesium sulfate and concentrated in a vacuum to obtain 132 g of a crude product. This crude product was purified by silica gel chromatography (ethyl acetate/hexane/formic acid=100:900:1) to obtain 127 g of a colorless oil. This oil was crystallized from n-hexane to obtain 115 g of the title compound as a white crystalline powder.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. washThe obtained mixture was washed with water
  4. extractionextracted with 750 ml
  5. washwashed with ether and chloroform successively
  6. extractionextracted with ethyl acetate (800 ml and 400 ml)
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in a vacuum
  10. customto obtain 132 g of a crude product
  11. customThis crude product was purified by silica gel chromatography (ethyl acetate/hexane/formic acid=100:900:1)

출처 및 근거

ORD 기록
ord-26a36cd4cab747589631ff038c03b702
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292901

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