Carbon Dioxide → alpha-Methoxycarbonyl-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetic acid

HRID 726467Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1([CH3:31])[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]2[CH:19]=[C:18]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:17]=[CH:16][C:15]1=2.[C:32](=[O:34])=[O:33].Cl>C1COCC1>[CH3:30][O:29][C:27]([CH:26]([C:18]1[CH:17]=[CH:16][C:15]2[C:14]([CH3:31])([CH3:13])[CH2:23][CH2:22][C:21]([CH3:24])([CH3:25])[C:20]=2[CH:19]=1)[C:32]([OH:34])=[O:33])=[O:28]

Participants

Conditions

Temperature: -78 °C

Procedure

2.1 ml (14.6 mmol) of diisopropylamine and 80 ml of TEP were introduced into a three-necked flask under a nitrogen stream. At -78° C., 5.8 ml (14.6 mmol) of n-butyllithium (2.5M) were added dropwise, the mixture was stirred for 30 minutes, then a solution of 3.2 g (12.2 mmol) of methyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetate dissolved in 80 ml of THF was added dropwise and the mixture was stirred for one hour. While maintained at -78° C., CO2 was introduced for 30 minutes and then the temperature was permitted to increase to -40° C. and the reaction medium was poured into a 5N hydrochloric acid solution. The mixture was extracted with ethyl acetate, the organic phase decanted, dried over magnesium sulfate and evaporated. 3.7 g (100%) of expected acid were recovered in the form of a slightly yellow oil.

Workup

additionwas added dropwise
stirringthe mixture was stirred for one hour
temperatureto increase to -40° C.
extractionThe mixture was extracted with ethyl acetate
customthe organic phase decanted
dry with materialdried over magnesium sulfate
customevaporated
custom3.7 g (100%) of expected acid were recovered in the form of a slightly yellow oil

Sources & evidence

ORD record: ord-9a0423ad4d4c4a51940cd2cd37de51c6
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05709867

Reaction notes

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