Aluminium lithium hydride → HCID 85471427, compound

HRID 2177381Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:18]=[C:17]([F:19])[S:16][C:15]=2[CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](OCC)=[O:31])=[C:24]([CH3:35])[C:23]=2[CH3:36])=[CH:10][CH:9]=1>>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:18]=[C:17]([F:19])[S:16][C:15]=2[CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][OH:31])=[C:24]([CH3:35])[C:23]=2[CH3:36])=[CH:10][CH:9]=1

Participants

Reactant 2

HCID 21226445Aluminium lithium hydride

HCID 90418004HCID 90418004, compound

Product 1

HCID 85471427HCID 85471427, compound

Procedure

The title compound was prepared according to the procedure described in Example 223 by LAH reduction of ethyl 3-(4-((3-(4-chlorophenyl)-5-fluorothiophen-2-yl)methoxy)-2,3-dimethyl phenyl)propanoate to give the desired product as off-white oil. 1H NMR (300 MHz, CD3OD) δ: 7.36-7.39 (m, 4H), 6.85 (d, J=8.4 Hz, 1H), 6.63 (s, 1H), 6.58 (d, J=8.1 Hz, 1H), 4.98 (s, 2H), 3.54 (t, J=6.3 Hz, 2H), 2.58-2.63 (m, 2H), 2.17 (s, 3H), 2.10 (s, 3H), 1.64-1.74 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C22H22ClFO2S, 403.1 (M−H). found 403.0.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-1fe8edc39d684ba98ad8ef87f48b9317
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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