Potassium Carbonate → Diethyl 4-[[[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl]thio]methyl]-1,3-dithiolane-2,2-dipropanoate

HRID 1650243Notes

Reaction equation

HRID 1650243 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C:7]1([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[S:11][CH:10]([CH2:12][SH:13])[CH2:9][S:8]1)[CH3:2].[CH2:22]([C:25]1[C:37]([OH:38])=[C:36]([C:39](=[O:41])[CH3:40])[CH:35]=[CH:34][C:26]=1[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]Br)[CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:39]([C:36]1[CH:35]=[CH:34][C:26]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][S:13][CH2:12][CH:10]2[CH2:9][S:8][C:7]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:21])[S:11]2)=[C:25]([CH2:22][CH2:23][CH3:24])[C:37]=1[OH:38])(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 137632981-Bromo-5-[2-n-propyl-3-hydroxy-4-acetylphenoxy]-pentaneHCID 14405949Diethyl-4-(mercaptomethyl)-1,3-dithiolane-2,2-dipropanoate

Product 1

HCID 14405909Diethyl 4-[[[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl]thio]methyl]-1,3-dithiolane-2,2-dipropanoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The title compound was prepared according to the procedure of Example 2 using the mercaptan produced in Example 31 (0.5 g, 0.0014 mol), 5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)-1-bromopentane (described in U.S. Pat. No. 4,565,882, Example 1) (0.484 g, 0.0014 mol) and anhydrous potassium carbonate (0.70 g) in methyl ethyl ketone (5 ml). The crude product was chromatographed on silica gel using 30% ethyl acetate/hexane as eluent to give 0.52 g (75%) of the product as an oil.

Workup

  1. customThe crude product was chromatographed on silica gel using 30% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-9e27aeed63094fa8852fa5012febb9f9
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

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