Hydrochloric Acid → 2-(4-Methyl-2-nitro phenyl)thiazol-4-yl methanol

HRID 227237ノート

反応式

HRID 227237 の反応式
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])[S:9][CH:10]=1)=O)C.[BH4-].[Na+].Cl>CCO>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[S:9][CH:10]=[C:6]([CH2:4][OH:3])[N:7]=2)=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 866229124-Methyl-2-nitro-phenyl-thiazole-4-carboxylic acid ethyl ester

生成物 1

HCID 690554642-(4-Methyl-2-nitro phenyl)thiazol-4-yl methanol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-(4-Methyl-2-nitro-phenyl-thiazole-4-carboxylic acid ethyl ester (292 mg, 1 mmol) was dissolved in 5 mL of absolute EtOH at room temperature in an open flask. Sodium borohydride (1 mmol, 38 mg) was added portionwise over several hours and the reaction was monitored by TLC (EtOAc:hexanes 2:3). After completion of the reaction, 2N HCl was added carefully with stirring. After 15 min, the clear yellow solution was concentrated on the rotavap, and the crude mixture was partitioned between EtOAc (60 mL) and water (60 mL). The organics were isolated and washed with sat NaHCO3 and 60 mL of sat NaCl. The organics were dried over MgSO4, filtered and concentrated to provide an orange solid as the desired material.

後処理

  1. additionwas added carefully
  2. concentrationthe clear yellow solution was concentrated on the rotavap
  3. customthe crude mixture was partitioned between EtOAc (60 mL) and water (60 mL)
  4. customThe organics were isolated
  5. washwashed with sat NaHCO3 and 60 mL of sat NaCl
  6. dry with materialThe organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-0e3cab60644d4dc58b90233874bdd655
出典データセット
uspto-grants-2009_07
特許番号
US07560462B2

反応ノート

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