Methyl chloroformate → Methyl 3-(4,4-dimethyl-chroman-6-yl)propiolate

HRID 428235Notes

Reaction equation

CC1(C)[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]([O:18][CH2:19]C)=[O:17])[CH:5]=[CH:4][C:3]1=2.CC1(C)C2C(=CC=C(C#C)C=2)[O:26]CC1.COC(Cl)=O.C([Li])CCC>>[CH3:12][C:9]1([CH3:13])[C:8]2[C:3](=[CH:4][CH:5]=[C:6]([C:14]#[C:15][C:16]([O:18][CH3:19])=[O:17])[CH:7]=2)[O:26][CH2:11][CH2:10]1

Participants

Reactant 4

HCID 6586Methyl chloroformate

HCID 11000580Ethyl 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)propiolate2×

HCID 156169944,4-Dimethyl-6-ethynylchroman

HCID 178418339Butyllithium

Product 1

HCID 18357965Methyl 3-(4,4-dimethyl-chroman-6-yl)propiolate

Procedure

Employing the same general procedure as used for the preparation of ethyl 3-[5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-naphth-2-yl]propiolate (Compound A) but instead using 1.86 g (10 mmols) of [4,4-dimethyl-chroman-6-yl]ethyne, 2 g (21.3 mmols) of methylchloroformate and 11 mmols of n-butyllithium the title compound was obtained as a yellow solid.

Sources & evidence

ORD record: ord-5d492df4c9b04e778690fd1e14a44670
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313163B1

Reaction notes

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