Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate → (2-Chloro-4-(trifluoromethyl)thiazol-5-yl)methanol

HRID 354724ノート

反応式

HRID 354724 の反応式
[Cl:1][C:2]1[S:3][C:4]([C:11](OCC)=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.C([BH3-])#N.[Na+].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[S:3][C:4]([CH2:11][OH:12])=[C:5]([C:7]([F:8])([F:9])[F:10])[N:6]=1

参加物

5

反応物 3

HCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylateHCID 4311764Sodium borohydrideHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 12953359(2-Chloro-4-(trifluoromethyl)thiazol-5-yl)methanol収率 74%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a mixture of 2.6 g (0.01 mol) of ethyl 2-chloro-4-(trifluoromethyl)-5-thiazolecarboxylate and 10 ml of ethanol was added 0.62 g of sodium cyanoborohydride. The reaction mixture was stirred for 5 minutes and 0.40 g of sodium borohydride was added. The temperature of the reaction mixture raised spontaneously to boiling point. The reaction mixture was stirred for 30 minutes and quenched with water. The aqueous mixture was extracted with ether. The ether solution was dried over CaSO4 and concentrated under reduced pressure. The residue was crystallized from petroleum ether to give 1.6 g (74%) of 2-chloro-4-(trifluoromethyl)-5-thiazolemethanol, mp 39°-45° C.

後処理

  1. temperatureThe temperature of the reaction mixture raised spontaneously
  2. stirringThe reaction mixture was stirred for 30 minutes
  3. customquenched with water
  4. extractionThe aqueous mixture was extracted with ether
  5. dry with materialThe ether solution was dried over CaSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from petroleum ether

出典と根拠

ORDレコード
ord-1cfabf648c5d4040808d98934a2d27c5
出典データセット
uspto-grants-1983_03
特許番号
US04377054

反応ノート

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