Trifluoroacetic acid → 2-{3-Methoxy-2-propoxy-5-[5-(3,4,5-trimethoxyphenyl)oxolan-2-yl]benzene-1-sulfonyl}ethan-1-ol

HRID 1085637Notes

Reaction equation

HRID 1085637 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[OH:8][CH2:9][CH2:10][S:11]([C:14]1[C:15](OCCC)=[C:16]([O:38][CH3:39])[CH:17]=[C:18]([CH:20](O)[CH2:21][CH2:22][CH:23]([C:25]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=2)[OH:24])[CH:19]=1)(=[O:13])=[O:12].[C:44]([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[OH:8][CH2:9][CH2:10][S:11]([C:14]1[C:15]([O:5][CH2:3][CH2:2][CH3:44])=[C:16]([O:38][CH3:39])[CH:17]=[C:18]([C@H:20]2[CH2:21][CH2:22][C@H:23]([C:25]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=3)[O:24]2)[CH:19]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 15718041HCID 15718041, compound

Product 1

HCID 1787172-{3-Methoxy-2-propoxy-5-[5-(3,4,5-trimethoxyphenyl)oxolan-2-yl]benzene-1-sulfonyl}ethan-1-ol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Trifluoroacetic acid (10%, v/v) in chloroform (500 mL) was added to a stirred 0° C. solution of 1-(5-(2-hydroxyethylsulfonyl)-4-n-propoxy-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl) butan-1,4-diol (75 g, 0.142 mole) in chloroform (500 mL). The temperature was slowly raised to room temperature and the mixture stirred for 3-4 hours. Anhydrous Na2CO3 (80 g, 0.75 mole) was added to this solution, and the mixture was stirred vigorously for 30 minutes. The solid was filtered off, and the filtrate was evaporated to a residue, which was purified by flash column chromatography on SiO2 eluted with hexane-ethyl acetate (6:1, v/v) to afford the desired trans isomer which is more mobile than the cis isomer. The product was recrystallized from methylene chloride-hexane to give of pure trans-2-(5-(2-hydroxyethylsulphonyl)-4-n-propoxy-3-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran, m.p. 141°-142° C. NMR (CDCl3) δ: 1.03 (t, J=7.8 Hz, CH2CH2CH3), 1.85 (m, CH2CH2CH3), 2.01, 2.46 (m, H-3 and H-4), 3.64 (m, SO2CH2CH2OH) 3.84, 3.86, 3.88 (35, 4 OCH3), 4.89 (m, SO2CH2CH2OH), 4.07 (t, J=8 Hz, OCH2CH2CH3), 5.13 (m, H-2 and H-5) 6.62 (s, Ar-H H-2 and H-6), 7.32 (d, J=2 Hz, Ar-H H-6), 7.52 (d, J=2 Hz, Ar-H H-2).

Workup

  1. stirringthe mixture was stirred vigorously for 30 minutes
  2. filtrationThe solid was filtered off
  3. customthe filtrate was evaporated to a residue, which
  4. customwas purified by flash column chromatography on SiO2
  5. washeluted with hexane-ethyl acetate (6:1
  6. customv/v) to afford the desired trans isomer which
  7. customThe product was recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-2a897cf2c33b496d95de57e11992da4f
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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