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

HRID 1290348Notes

Reaction equation

HRID 1290348 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 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.

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-21a570ace2494572b7657700c817556a
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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