Sodium Bicarbonate → 1-(7-Hydroxymethyl-benzofuran-5-yl)-ethanone

HRID 1584776노트

반응식

HRID 1584776 반응식
[C:1]([C:4]1[CH:5]=[C:6]([CH:13]=[O:14])[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[OH:14][CH2:13][C:6]1[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21220947HCID 21220947, 화합물

생성물 1

HCID 212208891-(7-Hydroxymethyl-benzofuran-5-yl)-ethanone수율 57.8%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 5-acetyl-benzofuran-7-carbaldehyde (471 mg) in dry toluene (40 ml) was treated with sodium triacetoxyborohydride (1.12 ml) and heated at reflux for 5.5 h. The reaction mixture was poured into 8% sodium bicarbonate (40 ml) and the phases were separated. The aqueous phase was extracted with ethyl acetate (40 ml), the combined organic phases were dried, filtered, and the filtrate evaporated in vacuo to give a yellow gum. Purification by FCC eluted with hexane:ethyl acetate (2:1→1:1) gave the title compound as a pale yellow oil (275 mg) which slowly solidified.

후처리

  1. temperatureheated
  2. temperatureat reflux for 5.5 h
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (40 ml)
  5. customthe combined organic phases were dried
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customto give a yellow gum
  9. customPurification by FCC
  10. washeluted with hexane:ethyl acetate (2:1→1:1)

출처 및 근거

ORD 기록
ord-708bb31745db4974a2a603adb9bad6f2
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05935972

반응 노트

불러오는 중…