Aluminium lithium hydride → HCID 85472980, compound

HRID 2177383Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl[C:8]1[S:12][C:11]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](OCC)=[O:24])=[C:17]([F:28])[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>>[CH2:36]([C:33]1[CH:32]=[CH:31][C:30]([C:10]2[CH:9]=[CH:8][S:12][C:11]=2[CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][OH:24])=[C:17]([F:28])[C:16]=2[F:29])=[CH:35][CH:34]=1)[CH3:37]

Participants

Reactant 2

HCID 21226445Aluminium lithium hydride

HCID 90418421HCID 90418421, compound

Product 1

HCID 85472980HCID 85472980, 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]-2,3-difluoro phenyl)propanoate to give the desired product as off-white oil. 1H NMR (300 MHz, CD3OD) δ7.41 (d, J=5.1 Hz, 1H), 7.30 (d, J=8.4 Hz, 2H), 7.20 (d, J=8.4 Hz, 2H), 7.08 (d, J=5.1 Hz, 1H), 6.82 (t, J=8.7 Hz, 1H), 6.68 (t, J=8.7 Hz, 1H), 5.14 (s, 2H), 3.53 (t, J=6.3 Hz, 2H), 2.59-2.66 (m, 4H), 1.70-1.80 (m, 2H), 1.23 (t, J=7.8 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H22F2O2S, 201.1[M-C9H9F2O2]. found 201.1.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-b4f09fe91c22434eb693ffb80d931f2e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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