5,5-Dimethyl-5,6,7,8-tetrahydro-2-naphthoyl chloride → Methyl 2-hydroxy-4-[3-oxo-3-(5,5-dimethyl-5,6,7,8-tetrahydro-2-naphthyl)-1-propynyl]benzoate

HRID 428221Notes

Reaction equation

HRID 428221 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12](Cl)=[O:13])[CH:5]=[CH:4][C:3]1=2.[OH:16][C:17]1[CH:26]=[C:25]([C:27]#[C:28][Si](C)(C)C)[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]>>[OH:16][C:17]1[CH:26]=[C:25]([C:27]#[C:28][C:12](=[O:13])[C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:15])([CH3:1])[CH2:11][CH2:10][CH2:9][C:8]=3[CH:7]=2)[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

3

Reactant 2

HCID 183578975,5-Dimethyl-5,6,7,8-tetrahydro-2-naphthoyl chlorideHCID 22641103Methyl 2-hydroxy-4-trimethylsilylethynylbenzoate

Product 1

HCID 18357916Methyl 2-hydroxy-4-[3-oxo-3-(5,5-dimethyl-5,6,7,8-tetrahydro-2-naphthyl)-1-propynyl]benzoate

Procedure

In a similar manner to Example 14(a), by reaction of 4.7 g (21 mmol) of 5,5-dimethyl-5,6,7,8-tetrahydro-2-naphthoyl chloride with 5.7 g (22.8 mmol) of methyl 2-hydroxy-4-trimethylsilylethynylbenzoate (prepared in Example 5(a) of patent EP 0,661,258), 5.14 g (68.5%) of the expected methyl ester are obtained, with a melting point of 89-90° C.

Workup

  1. customare obtained, with a melting point of 89-90° C.

Sources & evidence

ORD record
ord-7ba2df9de4fa4f5ea230851bc9ebd7c2
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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