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

HRID 1199726ノート

反応式

HRID 1199726 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-010d55eb04834467b77a1d56a9e94278
出典データセット
uspto-grants-1990_02
特許番号
US04902701

反応ノート

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