Aluminium lithium hydride → HCID 85473099, compound

HRID 2177374Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[S:12][C:11]([CH2:13][O:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([CH2:22][CH2:23][C:24](OCC)=[O:25])=[CH:17][C:16]=2[F:29])=[C:10]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][CH3:37])=[CH:32][CH:31]=2)[CH:9]=1>>[Cl:7][C:8]1[S:12][C:11]([CH2:13][O:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([CH2:22][CH2:23][CH2:24][OH:25])=[CH:17][C:16]=2[F:29])=[C:10]([C:30]2[CH:31]=[CH:32][C:33]([CH2:36][CH3:37])=[CH:34][CH:35]=2)[CH:9]=1

Participants

Reactant 2

HCID 21226445Aluminium lithium hydride

HCID 90418201HCID 90418201, compound

Product 1

HCID 85473099HCID 85473099, compound

Procedure

The title compound was prepared according to the procedure described in Example 223 by LAH reduction of ethyl 3-(4-((5-chloro-3-(4-ethylphenyl)thiophen-2-yl)methoxy)-3,5-difluoro phenyl)propanoate to give the desired product as off-white oil. 1H-NMR (300 MHz, CD3OD) δ 7.27 (d, J=8.4 Hz, 2H), 7.17 (d, J=8.4 Hz, 2H), 6.92 (s, 1H), 6.72 (t, J=8.4 Hz, 2H), 5.01 (s, 2H), 3.29 (t, J=6.6 Hz, 2H), 2.54-2.64 (m, 4H), 1.68-1.78 (m, 2H), 1.18 (t, J=7.8 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H21C1F2O2S, 235.0 (M-C9H9F2O2). found 235.0.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-3bcda0a02d674d6d8c973f1abd051e76
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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