Hydrogen Bromide → (R)-1-trichloromethyl-3-methyl-2-butenyl acetoacetate

HRID 127007Notes

Reaction equation

HRID 127007 reaction equation
C1([C@@H](N[C:14]([CH3:28])=[CH:15][C:16]([O:18][C@@H:19]([C:24]([Cl:27])([Cl:26])[Cl:25])[CH:20]=[C:21]([CH3:23])[CH3:22])=[O:17])C)C2C(=CC=CC=2)C=CC=1.Cl.Br.[N+]([O-])(O)=[O:32].OP(O)(O)=O.OS(O)(=O)=O>O1CCCC1>[C:16]([O:18][C@@H:19]([C:24]([Cl:27])([Cl:26])[Cl:25])[CH:20]=[C:21]([CH3:23])[CH3:22])(=[O:17])[CH2:15][C:14]([CH3:28])=[O:32]

Participants

8

Reactant 6

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 86737543(R)-3-methyl-1-trichloromethylbut-2-en-1-yl (S)-3-[N-(1-(1-naphthyl)ethyl)amino]but-2-enoate2×

Product 1

HCID 12525204(R)-1-trichloromethyl-3-methyl-2-butenyl acetoacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

hydrolyzing the recovered (R)-3-methyl-1-trichloromethylbut-2-en-1-yl (S)-3-[N-(1-(1-naphthyl)ethyl)amino]but-2-enoate in a mixture of tetrahydrofuran and aqueous mineral acid selected from HCl, HBr, HNO3, H3PO4, and H2SO4, about 1-20 equivalents of 0.1 to 4 N aqueous mineral acid being employed for each equivalent of (R)-3-methyl-1-trichloromethylbut-2-en-1-yl (S)-3-[N-(1-(1-naphthyl)ethyl)amino]but-2-enoate.

Sources & evidence

ORD record
ord-caf8b0f49bfd461ea47e9ab68abbf23b
Source dataset
uspto-grants-1981_03
Patent number
US04254279

Reaction notes

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