1-Bromo-5-[2-n-propyl-3-hydroxy-4-acetylphenoxy]-pentane → Diethyl 4-[[[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl]thio]methyl]-1,3-oxathiolane-2,2-dipropanoate

HRID 1383135Notes

Reaction equation

HRID 1383135 reaction equation
[SH:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:4]1.[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(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:1][CH2:2][CH:3]2[CH2:7][O:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:4]2)=[C:25]([CH2:22][CH2:23][CH3:24])[C:37]=1[OH:38])(=[O:41])[CH3:40]

Participants

4

Reactant 2

HCID 137632981-Bromo-5-[2-n-propyl-3-hydroxy-4-acetylphenoxy]-pentaneHCID 14405886Diethyl 4-(mercaptomethyl)-1,3-oxathiolane-2,2-dipropanoate

Product 1

HCID 14405889Diethyl 4-[[[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl]thio]methyl]-1,3-oxathiolane-2,2-dipropanoateYield 93%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of the mercaptan from Example 1 (2.0 g, 0.006 mol) and 5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)-1-bromopentane (described in U.S. Pat. No. 4,565,882, Example 1) (2.1 g. 0.06 mol) in methyl ethyl ketone (20 ml) was carried out and worked up in the same manner as described in Example 2. After chromatography on silica gel using 25% ethyl acetate/hexane as eluent, 3.3 g (93%) of the title compound was obtained as an oil.

Sources & evidence

ORD record
ord-c4e4942c5ffb4d5ba20cae47951cb3dc
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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