Ethyl 2-methyl-4,4,4-trifluoroacetoacetate → Ethyl 3-hydroxy-2-methyl-4,4,4-trifluorobutyrate

HRID 1458174ノート

反応式

HRID 1458174 の反応式
[O:1]=[C:2]([C:10]([F:13])([F:12])[F:11])[CH:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[BH4-].[Na+]>C(O)C>[OH:1][CH:2]([C:10]([F:11])([F:12])[F:13])[CH:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

参加物

4

反応物 2

HCID 2737204Ethyl 2-methyl-4,4,4-trifluoroacetoacetateHCID 4311764Sodium borohydride

生成物 1

HCID 533787Ethyl 3-hydroxy-2-methyl-4,4,4-trifluorobutyrate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of ethyl 3-keto-2-methyl-4,4,4-trifluorobutanoate (20.1 g, 0.10 moles) in 250 ml of absolute ethanol, cooled in an ice bath, was added sodium borohydride (1.0 g, 0.25 moles) in portions with stirring. The cooling bath was removed and the reaction stirred at room temperature for 30 minutes. Acetone (5 ml) was added to quench any remaining sodium borohydride and the solvents removed by distillation at atmospheric pressure using a Vigreaux column. The residue was diluted with 200 ml of methylene chloride and poured into a separatory funnel containing 75 ml of a 1:1:1 mixture of saturated ammonium chloride:brine:water. The layers were separated and the aqueous phase extracted with methylene chloride (3×25 ml). The combined organic phase and methylene chloride extracts were dried over magnesium sulfate, filtered and distilled at atmospheric pressure to remove the solvents. The residue was then distilled at reduced pressure (20 mmHg) using a Vigreaux column to give ethyl 3-hydroxy-2-methyl-4,4,4-trifluorobutanoate, bp 78°-84° C., 20 mmHg.

後処理

  1. customThe cooling bath was removed
  2. stirringthe reaction stirred at room temperature for 30 minutes
  3. additionAcetone (5 ml) was added
  4. customto quench any remaining sodium borohydride
  5. customthe solvents removed by distillation at atmospheric pressure
  6. additionThe residue was diluted with 200 ml of methylene chloride
  7. additionpoured into a separatory funnel
  8. additioncontaining
  9. addition75 ml of a 1:1:1 mixture of saturated ammonium chloride
  10. customThe layers were separated
  11. extractionthe aqueous phase extracted with methylene chloride (3×25 ml)
  12. dry with materialThe combined organic phase and methylene chloride extracts were dried over magnesium sulfate
  13. filtrationfiltered
  14. distillationdistilled at atmospheric pressure
  15. customto remove the solvents
  16. distillationThe residue was then distilled at reduced pressure (20 mmHg)

出典と根拠

ORDレコード
ord-b10d3cb9bb184b65a57f46c38be496e4
出典データセット
uspto-grants-1998_12
特許番号
US05849866

反応ノート

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