Hexane → Ethyl 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)propiolate

HRID 428230

Reaction equation

[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=2[CH:4]=1)#[CH:2].C([Li])CCC.CCCCCC.[CH2:28]([O:30][C:31](Cl)=[O:32])[CH3:29]>CCOCC>[CH3:13][C:9]1([CH3:14])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]2[CH:4]=[C:3]([C:1]#[C:2][C:31]([O:30][CH2:28][CH3:29])=[O:32])[CH:12]=[CH:11][C:10]1=2

Participants

Conditions

Temperature: -10 °C

Procedure

To a cold solution (−78° C.) of 2-ethynyl,5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (900 mgs, 4.3 mmols) in ether (20 ml) was added n-butyllithium in hexane (5.6 mmols). The mixture was stirred for 45 mins, and ethylchloroformate (1.3 g, 12 mmols) was added via syringe. Stirring was continued for 45 mins then the mixture was warmed gradually to −10° C. and quenched by adding sodium bicarbonate (NaHCO3) solution (10 ml). Diethyl ether (100 ml) was added, the organic phase washed with water (10 ml), brine (10 ml), and dried (MgSO4). The solvent was removed in vacuo. Purification of the residue over silicagel (5% ethylacetate in hexane) gave the title compound as a colorless oil.

Workup

stirringStirring
waitwas continued for 45 mins
customquenched
additionby adding sodium bicarbonate (NaHCO3) solution (10 ml)
additionDiethyl ether (100 ml) was added
washthe organic phase washed with water (10 ml), brine (10 ml)
dry with materialdried (MgSO4)
customThe solvent was removed in vacuo
customPurification of the residue over silicagel (5% ethylacetate in hexane)

Sources & evidence

ORD record: ord-3e8e7146651c4e688d91778793842f9c
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313163B1

Linked notes

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