Aluminium lithium hydride → 3-(4-((3-(4-Ethylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methoxy)-2,3,5-trifluorophenyl)propan-1-ol

HRID 2177251Notes

Reaction equation

HRID 2177251 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([CH2:20][O:21][C:22]3[C:27]([F:28])=[CH:26][C:25]([CH2:29][CH2:30][C:31](OCC)=[O:32])=[C:24]([F:36])[C:23]=3[F:37])=[C:18]([C:38]([F:41])([F:40])[F:39])[S:17][N:16]=2)=[CH:11][CH:10]=1)[CH3:8]>>[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([CH2:20][O:21][C:22]3[C:27]([F:28])=[CH:26][C:25]([CH2:29][CH2:30][CH2:31][OH:32])=[C:24]([F:36])[C:23]=3[F:37])=[C:18]([C:38]([F:39])([F:40])[F:41])[S:17][N:16]=2)=[CH:11][CH:10]=1)[CH3:8]

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90418846Ethyl 3-(4-((3-(4-ethylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methoxy)-2,3,5-trifluorophenyl)propanoate

Product 1

HCID 904179593-(4-((3-(4-Ethylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methoxy)-2,3,5-trifluorophenyl)propan-1-ol

Procedure

The title compound was prepared according to the procedure described in Example 111 by LAH reduction of ethyl 3-(4-((3-(4-ethylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methoxy)-2,3,5-trifluorophenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.75 (d, J=7.5 Hz, 2H), 7.84 (d, J=7.8 Hz, 2H), 6.76 (m, 1H), 3.70 (t, J=8.5 Hz, 2H), 2.74 (m, 4H), 1.85 (m, 2H), 1.52 (br, s, 1H), 1.27 (t, J=9.5 Hz, 3H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-78cefe21979448629fc2edd080552a46
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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