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

HRID 1290348ノート

反応式

HRID 1290348 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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 is added 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 the trans-isomer and 2.89 g of the cis-isomer.

後処理

  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

出典と根拠

ORDレコード
ord-21a570ace2494572b7657700c817556a
出典データセット
uspto-grants-1998_05
特許番号
US05750735

反応ノート

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