1-Bromopropane → HCID 15078318, compound

HRID 1196712Notes

Reaction equation

HRID 1196712 reaction equation
[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:18]2[CH2:22][CH2:21][C@H:20]([C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)[O:19]2)[CH:10]=[C:11]([OH:17])[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5].[CH3:35][CH2:36][CH2:37]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:18]2[CH2:22][CH2:21][C@H:20]([C:23]3[CH:24]=[C:25]([O:33][CH3:34])[C:26]([O:31][CH3:32])=[C:27]([O:29][CH3:30])[CH:28]=3)[O:19]2)[CH:10]=[C:11]([O:17][CH2:35][CH2:36][CH3:37])[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:5])=[O:6]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 15078317HCID 15078317, compound

Product 1

HCID 15078318HCID 15078318, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of trans-2-[3-(2-hydroxyethylsulfonyl)-4-n-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (366 mg, 0.74 mmol), n-propyl bromide (0.12 mL, 1.33 mmol) and potassium carbonate (255 mg, 1.85 mmol) in DMF (3 mL) was heated at 75° C. for 1 h. The reaction mixture was cooled and partitioned between ethyl ether and water, and the aqueous layer was re-extracted with ether (2 ×). The organic extracts were combined, dried, and evaporated to dryness. The residue was purified by chromatography to give the title compound: Rf 0.43 (hexane-ethyl acetate; 1:2, v/v); NMR (CDCl3) δ1.05 & 1.09 (2 t, J=7.5 Hz, 2 CH2CH2CH3), 2.85 (t, J=6.5 Hz, OH), 3.65 (m, SO2CH2), 3.95 (m, SO2CH2CH2), 4.03 & 4.15 (2 t, J=6.5 Hz, 2 CH2CH2CH3), 6.63 (s, 2 H, C5ArH), 7.27 & 7.49 (2 d, J=1.5 Hz, C2ArH).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl ether and water
  3. extractionthe aqueous layer was re-extracted with ether (2 ×)
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-603b966fcb1547afb1476cccbd03a488
Source dataset
uspto-grants-1992_05
Patent number
US05114961

Reaction notes

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