Trifluoroacetic acid → HCID 15078315, compound

HRID 1196711Notes

Reaction equation

HRID 1196711 reaction equation
[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([CH:25](O)[CH2:26][CH2:27][CH:28]([C:30]2[CH:35]=[C:34]([O:36][CH3:37])[C:33]([O:38][CH3:39])=[C:32]([O:40][CH3:41])[CH:31]=2)[OH:29])[CH:10]=[C:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:25]2[CH2:26][CH2:27][C@H:28]([C:30]3[CH:35]=[C:34]([O:36][CH3:37])[C:33]([O:38][CH3:39])=[C:32]([O:40][CH3:41])[CH:31]=3)[O:29]2)[CH:10]=[C:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:5])=[O:6]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 15078335HCID 15078335, compound

Product 1

HCID 15078315HCID 15078315, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-[3-(2-hydroxyethylsulfonyl)-4-propoxy-5-benzyloxyphenyl]-4-(3,4,5-trimethoxyphenyl)butan-1,4-diol (from previous experiment) in chloroform (20 mL) was treated with 10% trifluroacetic acid (20 mL). The reaction was monitored by TLC. After 1 h, anhydrous sodium carbonate was added, and the solid was filtered off and washed with chloroform. The solvent was evaporated and the residue was passed through a flash column of silica gel (hexane-ethyl acetate; 2:1, v/v). The cis- and trans-isomers were then separated by HPLC (hexane-ethyl acetate; 1:1, v/v): mp 112°-113° C.; Rf 0.33 (hexane-ethyl acetate; 1:1, v/v); NMR (CDCl3) δ0.98 (t, J=7.5 Hz, CH2CH2CH3), 1.83 (m, CH2CH2CH3), 2.85 (t , J=6.5 Hz, OH), 3.67 (q, SO2CH2), 3.98 (q, SO2CH2CH2), 4.17 (t, CH2CH2CH3), 5.18 (s, CH2C6H5), 6.63 (s, 2 e,uns/H/ , C5ArH).

Workup

  1. filtrationthe solid was filtered off
  2. washwashed with chloroform
  3. customThe solvent was evaporated
  4. customThe cis- and trans-isomers were then separated by HPLC (hexane-ethyl acetate

Sources & evidence

ORD record
ord-2047feb4feab4553a78c875f9fcd1237
Source dataset
uspto-grants-1992_05
Patent number
US05114961

Reaction notes

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