1,2-Dibromoethane → HCID 15078312, compound

HRID 1110831Notes

Reaction equation

HRID 1110831 reaction equation
[Br:1][CH2:2][CH2:3]Br.[OH:5][CH:6]([CH3:39])[CH2:7][S:8]([C:11]1[CH:12]=[C:13]([C@H:22]2[CH2:26][CH2:25][C@H:24]([C:27]3[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=3)[O:23]2)[CH:14]=[C:15]([OH:21])[C:16]=1[O:17][CH2:18][CH2:19][CH3:20])(=[O:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:5][CH:6]([CH3:39])[CH2:7][S:8]([C:11]1[CH:12]=[C:13]([C@H:22]2[CH2:26][CH2:25][C@H:24]([C:27]3[CH:28]=[C:29]([O:37][CH3:38])[C:30]([O:35][CH3:36])=[C:31]([O:33][CH3:34])[CH:32]=3)[O:23]2)[CH:14]=[C:15]([O:21][CH2:3][CH2:2][Br:1])[C:16]=1[O:17][CH2:18][CH2:19][CH3:20])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 15078298HCID 15078298, compound

Product 1

HCID 15078312HCID 15078312, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1,2-Dibromoethane (1.12 mL, 13 mmol) was added to a solution of trans-2-[3-(2-hydroxypropylsulfonyl)-4-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (331 mg, 0.65 mmol) in DMF (5 mL) containing potassium carbonate (550 mg, 3.9 mmoI). The reaction mixture was heated with stirring at 70° C. for 7 h and, 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 dryness. The product was purified by flash column chromatography on silica gel using hexane-ethyl acetate (2:1, v/v) as the eluant Rf 0.42 (hexane-ethyl acetate; 1:2, v/v); NMR (CDCl3) δ 1.06 (t, CH2CH2CH3), 1.25 (d, CH2CHOHCH3), 1.90 (m, CH2CH2CH3), 3.74 (t, CH2CH2Br), 3.83 (s. OCH3 ), 3.88 (s. 2OCH3). 5.16-5.28 (m, H-2 & H-5), 6.62 (s. 2H, C5ArH), 7.28 and 7.54 (2d, 2H, C2ArH).

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 dryness
  8. customThe product was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-112caa213cbe464fb25b452a97b185b6
Source dataset
uspto-grants-1990_12
Patent number
US04977146

Reaction notes

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