1,3-Dibromopropane → HCID 15078313, compound

HRID 1196701Notes

Reaction equation

HRID 1196701 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.[OH:6][CH:7]([CH3:40])[CH2:8][S:9]([C:12]1[CH:13]=[C:14]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[O:24]2)[CH:15]=[C:16]([OH:22])[C:17]=1[O:18][CH2:19][CH2:20][CH3:21])(=[O:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:6][CH:7]([CH3:40])[CH2:8][S:9]([C:12]1[CH:13]=[C:14]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:29]=[C:30]([O:38][CH3:39])[C:31]([O:36][CH3:37])=[C:32]([O:34][CH3:35])[CH:33]=3)[O:24]2)[CH:15]=[C:16]([O:22][CH2:4][CH2:3][CH2:2][Br:1])[C:17]=1[O:18][CH2:19][CH2:20][CH3:21])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 15078298HCID 15078298, compound

Product 1

HCID 15078313HCID 15078313, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1,3-Dibromopropane (0.105 mL, 1.0 mol) was added to a solution of trans-2-[3-(2-hydroxypropylsulfonyl)-4-n-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (102 mg, 0.20 mmol) in DMF (1 mL) containing potassium carbonate (105 mg, 0.76 mmol). The reaction mixture was heated with stirring under nitrogen at 70° C. for 2 h, cooled, and partitioned between ethyl ether and water. The ethereal layer was separated and the aqueous layer was re-extracted twice with ether. The organic extracts were combined, dried, and evaporated to a residue (143 mg). Purification by preparative TLC (hexane-ethyl acetate; 1:1, v/v) gave the title compound as a colorless foam; Rf 0.5; NMR (CDCl3) δ 1.26 (d, CH2CHOHCH3), 3.66 (t, CH2Br).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturecooled
  3. custompartitioned between ethyl ether and water
  4. customThe ethereal layer was separated
  5. extractionthe aqueous layer was re-extracted twice with ether
  6. customdried
  7. customevaporated to a residue (143 mg)
  8. customPurification by preparative TLC (hexane-ethyl acetate

Sources & evidence

ORD record
ord-09e6cfc7d6e74e6aa40db6558f8fbf55
Source dataset
uspto-grants-1992_05
Patent number
US05114961

Reaction notes

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