Bromoacetic Acid → 4-(2-Furyl)-3-oxaoctanoic acid

HRID 274427

반응식

HRID 274427 반응식
[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C@@H:8]([OH:13])[CH2:9][CH2:10][CH2:11][CH3:12].Br[CH2:15][C:16]([OH:18])=[O:17]>C1COCC1>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]([CH2:9][CH2:10][CH2:11][CH3:12])[O:13][CH2:15][C:16]([OH:18])=[O:17]

참가 물질

5

반응물 3

HCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 54324361(S)-1-(2-Furyl)-1-pentanol

생성물 1

HCID 197960084-(2-Furyl)-3-oxaoctanoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

NaH (16.3 g, 680.9 mmol) and freshly distilled THF (170 mL) were stirred at room temperature as (S)-1-(2-furyl)-1-pentanol ([α]25D -17.2°, 30.0 g, 46.0 mmol) in THF (170 mL) was added dropwise. After the addition was complete, the mixture was stirred for 15 m before cautiously heating to reflux for 1 h. The mixture was cooled to 0° C. before adding dropwise a solution of bromoacetic acid (27.3 g, 196.5 mmol) in THF (40 mL). The mixture was refluxed 2 days before cooling and carefully pouring into 600 mL ice water. The aqueous was washed with ether and acidified with HCl to pH 4, and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4, and evaporated to give a quantitative yield of crude product which was used in the next step without further purification.

후처리

  1. additionwas added dropwise
  2. additionAfter the addition
  3. temperaturebefore cautiously heating
  4. temperatureto reflux for 1 h
  5. temperatureThe mixture was refluxed 2 days
  6. temperaturebefore cooling
  7. washThe aqueous was washed with ether
  8. extractionextracted with ether
  9. washThe combined organic extracts were washed with brine
  10. dry with materialdried over MgSO4
  11. customevaporated

출처 및 근거

ORD 기록
ord-09a34f56bee543a6ba1ae309abfdb22d
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389647

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