Water → 7-(Methylsulfanyl)-9H-xanthene-3-carbaldehyde

HRID 1199726노트

반응식

HRID 1199726 반응식
C(Cl)(=O)C(Cl)=O.[CH3:7][S:8][C:9]1[CH:22]=[CH:21][C:20]2[O:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:23][OH:24])[CH:17]=3)[CH2:12][C:11]=2[CH:10]=1.C(N(CC)CC)C.O>C(Cl)Cl.CS(C)=O.C(OCC)(=O)C>[CH3:7][S:8][C:9]1[CH:22]=[CH:21][C:20]2[O:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH:23]=[O:24])[CH:17]=3)[CH2:12][C:11]=2[CH:10]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19865558[7-(Methylsulfanyl)-9H-xanthen-3-YL]methanol

생성물 1

HCID 198655577-(Methylsulfanyl)-9H-xanthene-3-carbaldehyde

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매2회HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Under dry nitrogen, dimethylsulphoxide (5 ml) was added dropwise to a stirred solution of oxalyl chloride (0.89 ml) in methylene chloride (5 ml) at -60° C. After 2 minutes a solution of the xanthene from step (A) (2.3 g) in dimethylsulphoxide (35 ml) was introduced dropwise over 5 minutes whilst maintaining the temperature below -50° C. with cooling. After 15 minutes triethylamine (6.20 ml) was added, the mixture allowed to warm to room temperature and then poured into water. The mixture was ethyl acetate extracted, the organic layers were combined, washed with brine, dried over magnesium sulphate and evaporated yielding the title carboxaldehyde (1.97 g), m.p. 122°-123° C.

후처리

  1. temperaturewhilst maintaining the temperature below -50° C.
  2. temperaturewith cooling
  3. extractionextracted
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customyielding the title carboxaldehyde (1.97 g), m.p. 122°-123° C.

출처 및 근거

ORD 기록
ord-010d55eb04834467b77a1d56a9e94278
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04902701

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