N-Methoxy-N-methylhexanamide → HCID 22640688, compound

HRID 899276Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])([CH3:12])[CH2:7][CH2:8][S:9]2)=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:22](=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C1COCC1>[CH3:12][C:6]1([CH3:13])[C:5]2[C:10](=[CH:11][C:2]([C:22](=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:3][CH:4]=2)[S:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 7-bromo-4,4-dimethyl-thiochroman (2.0 g, 7.78 mmole) in 45 mL of THF at −78° C. was, treated with 3.9 mL of 2.5M butyllithium. After 30 minutes at −78° C. a solution of hexanoic acid methoxy-methyl-amide (1.486 g, 9.33 mmole) in 5 mL of THF was added. The reaction mixture was stirred at −78° C. for 30 minutes, warmed to room temperature, quenched by the addition of 50 mL of saturated aqueous ammonium chloride solution and extracted with three 50 mL portions of ether. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 3% ethyl acetate in hexanes) to yield 1.183 g of 1-(4,4-dimethyl-thiochroman-7-yl)-hexan-1-one as a pale yellow oil.

Workup

customat −78° C.
temperaturewarmed to room temperature
customquenched by the addition of 50 mL of saturated aqueous ammonium chloride solution
extractionextracted with three 50 mL portions of ether
dry with materialThe combined organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a yellow oil
customThe product was purified by flash chromatography (SiO2, 3% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-cc88bd51380d483689cd99f482318130
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354931B2

Reaction notes

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