Diethyl Ether → HCID 15078330, compound

HRID 1110840Notes

Reaction equation

HRID 1110840 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].Cl[CH2:36][C:37](=[O:39])[CH3:38].C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CN(C=O)C.O>[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][CH2:36][C:37](=[O:39])[CH3:38])[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:5])=[O:6]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 15078317HCID 15078317, compound

Product 1

HCID 15078330HCID 15078330, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of trans-2-[3-(2-hydroxyethylsulfonyl)-4-n-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (183 mg, 0.37 mmol), chloroacetone (0.033 mL, 0.41 mmol) and potassium carbonate (162 mg, 1.17 mmol) in DMF (3 mL) was stirred at room temperature overnight. Ethyl ether and water were added and the aqueous layer was re-extracted with ether (2 x). The organic extracts were combined, dried, and evaporated to a syrup, which was purified by preparative TLC (hexane-ethyl acetate; 1:2, v/v) to give the title compound Rf 0.33; NMR (CDCl3) δ 1.06 (t, CH2CH2CH3), 2.33 (s, CH2COCH3), 3.66 (q, SO2CH2CH2), 3.97 (b, SO2CH2CH2) 4.20 (t, CH2CH2CH3), 4.68 (s, CH2COCH3), 5.12-5.28 (m, H-2 & H-5), 6.62 (s, 2 H, C5ArH), 7.17 & 7.56 (2 d, 2 H, C2ArH).

Workup

  1. extractionthe aqueous layer was re-extracted with ether (2 x)
  2. customdried
  3. customevaporated to a syrup, which
  4. customwas purified by preparative TLC (hexane-ethyl acetate

Sources & evidence

ORD record
ord-909209c40b8a4622bc6c43ff849827db
Source dataset
uspto-grants-1990_12
Patent number
US04977146

Reaction notes

Loading…