Aluminium lithium hydride → HCID 85473228, compound

HRID 2177378Notes

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[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31](OCC)=[O:32])=[C:25]([F:36])[C:24]=2[F:37])=[CH:11][CH:10]=1)[CH3:8]>>[CH2:7]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:19]=[C:18]([F:20])[S:17][C:16]=2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][OH:32])=[C:25]([F:36])[C:24]=2[F:37])=[CH:13][CH:14]=1)[CH3:8]

Participants

Reactant 2

HCID 21226445Aluminium lithium hydride

HCID 90418340HCID 90418340, compound

Product 1

HCID 85473228HCID 85473228, 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)-2,3-difluoro phenyl)propanoate to give the desired product as off-white oil. 1HNMR (300 MHz, CD3OD) δ 7.25-7.42 (m, 4H), 6.93 (t, J=8.4 Hz, 1H), 6.73 (t, J=8.4 Hz, 1H), 6.70 (s, 2H), 5.12 (s, 2H), 3.58 (t, J=7.5 Hz, 2H), 2.65-2.78 (m, 4H), 1.76-1.86 (m, 2H), 1.32 (t, J=7.8 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H21F3O2S, 405.1 (M−H). found 405.1.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-fc4619b171c6488483920904667daa4a
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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