Acetic Acid → HCID 58687907、化合物

HRID 1988573ノート

反応式

HRID 1988573 の反応式
[N:1]1([C:7]2[O:12][C:11]([C:13]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:14]=3[S:15][C:16]3[CH:17]=[CH:18][C:19]([CH:27]=[O:28])=[CH:20][C:21]=3[CH2:22]4)=[CH:10][C:9](=[O:29])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([BH3-])#N.[Na+].C(O)(=O)C>C(O)C>[OH:28][CH2:27][C:19]1[CH:20]=[C:21]2[C:16]([S:15][C:14]3[C:13]([C:11]4[O:12][C:7]([N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)=[CH:8][C:9](=[O:29])[CH:10]=4)=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:22]2)=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 176Acetic Acid2 回HCID 5003444Sodium cyanoborohydrideHCID 58687906HCID 58687906、化合物

生成物 1

HCID 58687907HCID 58687907、化合物収率 84%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of 5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthene-2-carbaldehyde (2)(0.392 g, 0.97 mmol) in ethanol (7 mL) at room temperature was added sodium cyanoborohydride (121 mg, 1.93 mmol), followed by the addition of acetic acid (1 mL). After 5 hours, a second addition of acetic acid (1 mL) was made. After a further 12 hours, the excess borohydride was quenched with acetone. After evaporation in vacuo, saturated NaHCO3 was added, followed by extraction into dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The brown coloured solid was dried under vacuum at 50° C. to give the crude title compound (0.332 g, 84%) which was used without any further purification. m/z (LC-MS, ESP), RT=3.09 min, (M++1)=408.3

後処理

  1. waitAfter a further 12 hours
  2. customthe excess borohydride was quenched with acetone
  3. customAfter evaporation in vacuo, saturated NaHCO3
  4. additionwas added
  5. extractionfollowed by extraction into dichloromethane
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe brown coloured solid was dried under vacuum at 50° C.

出典と根拠

ORDレコード
ord-3a6ec440699d49bead9bc9ecb44e0a4c
出典データセット
uspto-grants-2010_01
特許番号
US07642254B2

反応ノート

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