Potassium Carbonate → 2-[3-(2-Oxopropylsulfonyl)-4-n-propoxy 5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydro-furan

HRID 1110828Notes

Reaction equation

HRID 1110828 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.BrCCCN(C)C.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[O:1]=[C:2]([CH3:35])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([CH:18]2[CH2:22][CH2:21][CH: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]([OH:17])[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:5])=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12440776(3-Bromo-propyl)-dimethyl-amine hydrochlorideHCID 15078290trans-2-[3-(2-Oxopropylsulfonyl)-4-propoxy-5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

Product 1

HCID 198991462-[3-(2-Oxopropylsulfonyl)-4-n-propoxy 5-hydroxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydro-furan

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 300 mg of trans 2-[3-(2-oxo-propylsulfonyl)-4-n-propoxy-5- hydroxyphenyl]5-(3,4,5-trimethoxyphenyl)tetrahydrofuran, 6 mL acetone, 150 mg 3-bromopropyl- N,N-dimethylamine hydrochloride, and 150 mg K2CO3 was heated at 50° for 16 hrs and filtered. Evaporation of the filtrate and purification by prep. TLC on silica plates (ethyl acetate) gave the title compound as a colorless gum: NMR (200 MHz, CDCl3) δ 1.06 (t, CH2CH2CH3), 1.88 (m, CH2CH2CH3), 2.39 (s, CH3C(O)CH2), 2.30 (s, N(CH3)2), 2.40-2.58 (m, CH2N(CH)2)2, 3.85 (s, OCH3), 3.88 (s, 2 OCH3), 4.12 & 4.15 (t, 2 ArOCH2), 4.46 (s, CH3C(O)CH2), 5.10-5.30 (m, 2-CH & 5 -CH), 6.62 (s, 5-ArH), 7.30 & 7.44 (2 d, 2-ArH).

Workup

  1. temperaturewas heated at 50° for 16 hrs
  2. filtrationfiltered
  3. customEvaporation of the filtrate and purification by prep

Sources & evidence

ORD record
ord-fc6d48092fb94fd59eb1235b6980d84d
Source dataset
uspto-grants-1990_12
Patent number
US04977146

Reaction notes

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