Calcium Bromide → cis-(+/-)-4-Bromotetrahydro-2-[(phenylmethoxy)methyl]furan

HRID 1600089노트

반응식

HRID 1600089 반응식
[Br:1][CH:2]([CH2:15]Br)[CH2:3][CH:4]([OH:14])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Ca+2].[OH-].[Br-].[Ca+2].[Br-]>CO.O>[Br:1][C@H:2]1[CH2:15][O:14][C@@H:4]([CH2:5][O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3]1

참가 물질

6

반응물 3

HCID 5360316Calcium BromideHCID 6093208Calcium HydroxideHCID 110355494,5-Dibromo-1-(phenylmethoxy)-2-pentanol

생성물 1

HCID 11086853cis-(+/-)-4-Bromotetrahydro-2-[(phenylmethoxy)methyl]furan수율 93.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A solution of 10.0 g of product from Example 3 in 25 ml of methyl alcohol is diluted with 50 ml of distilled water. To this heterogeneous mixture isadded 1.6 g of calcium hydroxide followed by 16.95 g of calcium bromide. The reaction is stirred vigorously while heating in an oil bath, at 100° C., for 24 hours. The internal temperature is maintained at 85° C. The reaction is cooled, extracted with methylene chloride, filtered thru diatomaceous earth and the layers partitioned. The organic layer is washed with water and saturated sodium chloride, dried and concentrated in vacuo to give 7.18 g of an oil. The oil is purified by chromatography (Silica Gel: 5% ethyl acetate/hexane) to give 2.82 g of thetrans-isomer and 2.89 g of the cis-isomer.

후처리

  1. temperatureThe internal temperature is maintained at 85° C
  2. temperatureThe reaction is cooled
  3. extractionextracted with methylene chloride
  4. filtrationfiltered
  5. customthe layers partitioned
  6. washThe organic layer is washed with water and saturated sodium chloride
  7. customdried
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-792d800ae6cc41849ec8bb1b277b76b4
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05744465

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