2-Bromopropane → HCID 59419921, compound

HRID 587917Notes

Reaction equation

HRID 587917 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)[CH3:2].CO[C:19]1C=C(CC#N)C=[CH:23][C:24]=1OC.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32].[Br:36]C(C)C.C([N-]C(C)C)(C)C.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[H-].[Na+]>>[Br:36][CH2:23][CH2:24][CH2:19][C:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:4]([O:3][CH2:1][CH3:2])=[O:16]

Participants

8

Reactant 7

HCID 63582-BromopropaneHCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 667273,4-DimethoxybenzeneacetonitrileHCID 87441Ethyl 3,4-dimethoxyphenylacetateHCID 2724254Sodium bis(trimethylsilyl)amide2×HCID 2724682Lithium diisopropylamide

Product 1

HCID 59419921HCID 59419921, compound

Procedure

For Step 1, (3,4-dimethoxy-phenyl)-acetic acid ethyl 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-fe273c7d3ece4bedade145579cbc2a75
Source dataset
uspto-grants-2016_01
Patent number
US09227918B2

Reaction notes

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