2-Bromopropane → HCID 59419925, compound

HRID 587916Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.CO[C:18]1C=C(CC#N)C=[CH:22][C:23]=1OC.Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31].[Br:35]C(C)C.C([N-]C(C)C)(C)C.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[H-].[Na+]>>[Br:35][CH2:22][CH2:23][CH2:18][C:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)([C:3]([O:2][CH3:1])=[O:15])[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

Reactant 7

HCID 63582-Bromopropane

HCID 10928Ethyl chloroformate

HCID 24758Sodium hydride

HCID 667273,4-Dimethoxybenzeneacetonitrile

HCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl ester

HCID 2724254Sodium bis(trimethylsilyl)amide2×

HCID 2724682Lithium diisopropylamide

Product 1

HCID 59419925HCID 59419925, compound

Procedure

For Step 1, (3,4-dimethoxy-phenyl)-acetic acid methyl ester was substituted for (3,4-Dimethoxyphenyl)acetonitrile, ethyl chloroformate was substituted for 2-bromopropane and lithium diisopropylamide (LDA) was substituted for NaHMDS. For Step 2, sodium hydride was substituted for NaHMDS.

Sources & evidence

ORD record: ord-7d69c97a1f684856baa8c2bcb96b6b3d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227918B2

Reaction notes

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