Ethyl 2,2-dimethyl-3-(4-sulfanylphenyl)propanoate → HCID 11588493, compound

HRID 2355787Notes

Reaction equation

HRID 2355787 reaction equation
C(OC(=O)C(C)(C)CC1C=CC(S)=CC=1)C.[CH2:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([C:28]1[CH:33]=[CH:32][C:31]([C:34]([OH:40])([CH3:39])[C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH3:18]>>[CH2:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([C:28]1[CH:33]=[CH:32][C:31]([C@@:34]([OH:40])([CH3:39])[C:35]([F:36])([F:38])[F:37])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH3:18]

Participants

3

Reactant 2

HCID 4114055Ethyl 2,2-dimethyl-3-(4-sulfanylphenyl)propanoateHCID 52941221HCID 52941221, compound

Product 1

HCID 11588493HCID 11588493, compound

Procedure

Using the methods described above in Example 12, but substituting 2-ethylbenzenethiol for 3-(4-mercaptophenyl)-2,2-dimethylpropionic acid ethyl ester in step a, 2-[4-(2-ethylbenzenesulfonyl)phenyl]-1,1,1-trifluoropropan-2-ol was prepared. 1H NMR (CDCl3, 400 MHz) δ 8.19 (dd, J=1.3 Hz, 8.0 Hz, 1H), 7.84 (d, J=8.5 Hz, 2H), 7.73 (d, J=8.5 Hz, 2H), 7.56 (m, 1H), 7.40 (m, 1H), 7.32 (d, J=7.6 Hz 1H), 3.03 (s, 1H), 2.58 (q, J=7.4 Hz, 2H), 1.77 (s, 3H), 1.03 (t, J=7.5 Hz, 3H). The racemic product was resolved by chiral HPLC. The flow rate was 20 mL/min on a Chiralcel OD-H 20 mm i.d.×250 mm, 5μ column (Daciel Chemical Industries LTD), using isopropyl alcohol/hexanes (7/93) as the eluent.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-9970e5b162f741f8bb8a0649d00bcddb
Source dataset
uspto-grants-2010_07
Patent number
US07754890B2

Reaction notes

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