Aluminium lithium hydride → 3-(4-((3-(4-Ethylphenyl)-5-methylthiophen-2-yl)methoxy)-3,5-difluorophenyl)propan-1-ol

HRID 2177386Notes

Reaction equation

HRID 2177386 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH3:20])[S:17][C:16]=2[CH2:21][O:22][C:23]2[C:28]([F:29])=[CH:27][C:26]([CH2:30][CH2:31][C:32](OCC)=[O:33])=[CH:25][C:24]=2[F:37])=[CH:11][CH:10]=1)[CH3:8]>>[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH3:20])[S:17][C:16]=2[CH2:21][O:22][C:23]2[C:28]([F:29])=[CH:27][C:26]([CH2:30][CH2:31][CH2:32][OH:33])=[CH:25][C:24]=2[F:37])=[CH:11][CH:10]=1)[CH3:8]

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90418817Ethyl 3-(4-((3-(4-ethylphenyl)-5-methylthiophen-2-yl)methoxy)-3,5-difluorophenyl)propanoate

Product 1

HCID 854733623-(4-((3-(4-Ethylphenyl)-5-methylthiophen-2-yl)methoxy)-3,5-difluorophenyl)propan-1-ol

Procedure

The title compound was prepared according to the procedure described in Example 223 by LAH reduction of ethyl 3-(4-((3-(4-ethylphenyl)-5-methylthiophen-2-yl)methoxy)-3,5-difluoro phenyl)propanoate to give the desired product as off-white oil. 1H NMR (400 MHz, CDCl3) δ 7.35 (d, J=7.0 Hz, 2H), 7.24 (d, J=7.1 Hz, 2H), 6.78 (s, 1H), 6.72 (d, J=7.8 Hz, 2H), 5.11 (s, 2H), 3.72 (t, J=8.1 Hz, 2H), 2.72 (m, J=5.2 Hz, 2H), 2.65 (m, J=7.5 Hz, 2H), 2.49 (s, 3H), 1.82 (m, J=5.8 Hz, 2H), 1.70 (br, s, 1H), 1.28 (t, J=7.2 Hz, 3H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d7fc0e2c200641f8ad2f7fcbb2ce815f
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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