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

HRID 1600089Notes

Reaction equation

HRID 1600089 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-792d800ae6cc41849ec8bb1b277b76b4
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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