Chloroacetone → trans-2-[3-(2-Oxopropyl-sulfonyl)-4-n-propoxy-5-(2-oxopropoxy)phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

HRID 1110830Notes

Reaction equation

HRID 1110830 reaction equation
[O:1]=[C:2]([CH3:35])[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[CH2:37][C:38](=[O:40])[CH3:39].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)C>[O:1]=[C:2]([CH3:35])[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][CH2:37][C:38](=[O:40])[CH3:39])[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:5])=[O:6]

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 15078290trans-2-[3-(2-Oxopropylsulfonyl)-4-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

Product 1

HCID 9894129trans-2-[3-(2-Oxopropyl-sulfonyl)-4-n-propoxy-5-(2-oxopropoxy)phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of trans-2-[3-(2- oxopropylsulfonyl)-4-n-propoxy-5-hydroxyphenyl]5- (3,4,5-trimethoxyphenyl)tetrahydrofuran (51 mg, 0.1 mmol), chloroacetone(16 uL, 0.2 mmol) and potassium carbonate (28 mg, 0.2 mmol) in DMF (1 mL) was stirred at room temperature for 40 h. The reaction mixture was diluted with ethyl ether and washed with water and brine. The organic extracts were dried (MgSO4), filtered, and evaporated to a residue (58 mg), which was purified by preparative TLC (hexane ethyl acetate; 3:2. v/v). The title compound was isolated as a colorless foam: Rf 0.38; MS, m/z 564M+.; NMR (CDCl3) δ 1.08(t, CH2CH2CH3), 2.33 & 2.38 (2 s, OCH2COCH3 & SO2CH2COCH3), 4.48 (s, SO2CH2), 4.68 (s, OCH2CO), 5.20 (m, H-2 & H-5), 6.62 (s, 2 H, C5ArH), 7.20 & 7.52 (2 d, 2 H, C2ArH)

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to a residue (58 mg), which
  5. customwas purified by preparative TLC (hexane ethyl acetate; 3:2. v/v)

Sources & evidence

ORD record
ord-eec399f8945d4ac28f550aa416db8547
Source dataset
uspto-grants-1990_12
Patent number
US04977146

Reaction notes

Loading…