Sodium borohydride → Tetrahydro-2H-pyran-3-ethanol

HRID 1010940노트

반응식

HRID 1010940 반응식
[BH4-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][CH:10]=[O:11])[CH2:4]1>C(O)C>[O:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][CH2:10][OH:11])[CH2:4]1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 55264769Tetrahydro-2H-pyran-3-acetaldehyde

생성물 1

HCID 55264768Tetrahydro-2H-pyran-3-ethanol

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
50 °C

실험 절차

A suspension of sodium borohydride (554 mg) in ethanol (20 ml) was cooled (ice bath) and a solution of tetrahydro-2H-pyran-3-ylacetaldehyde (1.88 gm) in ethanol (8 ml) added dropwise with stirring over 10 min. After 15 min the ice bath was removed and after a further 3 h the mixture was heated at 50° C. for 1 h. After cooling the solvent was evaporated and the residue treated with water and extracted three times with dichloromethane. The combined extracts were washed with dilute brine, dried by passing through a hydrophobic frit and evaporated to give the title product as an oil. A further batch of product was obtained by acidifying the aqueous solution with 2N hydrochloric acid, saturating with sodium chloride and extracting three times with dichloromethane. These extracts were treated as above and the batches combined to give a total yield of 1.54 g (81%).

후처리

  1. temperaturewas cooled (ice bath)
  2. customAfter 15 min the ice bath was removed and after a further 3 h the mixture
  3. temperatureAfter cooling the solvent
  4. customwas evaporated
  5. additionthe residue treated with water
  6. extractionextracted three times with dichloromethane
  7. washThe combined extracts were washed with dilute brine
  8. customdried
  9. customevaporated

출처 및 근거

ORD 기록
ord-1f6ef8a63a014b0ba1a95eed208de9e5
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977344B2

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