Aluminium lithium hydride → HCID 85473365, compound

HRID 2177379Notes

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]([F: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]([F:20])[S:17][C:16]=2[CH2:21][O:22][C:23]2[C:24]([F:37])=[CH:25][C:26]([CH2:30][CH2:31][CH2:32][OH:33])=[CH:27][C:28]=2[F:29])=[CH:11][CH:10]=1)[CH3:8]

Participants

Reactant 2

HCID 21226445Aluminium lithium hydride

HCID 90418594HCID 90418594, compound

Product 1

HCID 85473365HCID 85473365, compound

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-fluorothiophen-2-yl)methoxy)-3,5-difluoro phenyl)propanoate to give the desired product as off-white oil. 1HNMR (300 MHz, CD3OD) δ 7.37 (d, J=8.1 Hz, 2H), 7.26 (d, J=8.1 Hz, 2H), 6.81 (t, J=9.3 Hz, 1H), 6.63 (s, 2H), 5.01 (s, 2H), 3.58 (t, J=6.0 Hz, 2H), 2.63-2.74 (m, 4H), 1.77-1.87 (m, 2H), 1.28 (t, J=7.8 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H21F3O2S, 219.1[M-C9H9F2O2]. found 219.1.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-211a0a1b73a246a381d15f0f00e11879
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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