Dimethylformamide → HCID 14155579, compound

HRID 649193Notes

Reaction equation

[CH2:1]([CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:26]=[O:27]>O1CCCC1>[CH2:1]([CH:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([CH:26]=[O:27])[CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-Benzyl-6-bromo-1,2,3,4-tetrahydronaphthalene (1.5 g, 0.005 mol) was dissolved in 30 ml tetrahydro-furan and cooled to -78° C. under dry N2. Butyl lithium (2.32 ml of 2.14 M in hexane, 0.005 mol) was added and the mixture stirred at -70° C. for 1 hour. Dimethyl-formamide (0.39 ml, 0.005 mol) was then added dropwise and the mixture stirred at -70° C. for 2 hours, allowed to warmed toward room temperature for 0.5 hour, poured slowly into 38 ml of ice cold 1N HCl and extracted 2×50 ml ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and stripped in vacuo to yield title product as an oil, 1.26 g; tlc Rf 0.6 (4:1 hexane:ethyl acetate).

Workup

stirringthe mixture stirred at -70° C. for 2 hours
temperatureallowed to warmed toward room temperature for 0.5 hour
extractionextracted 2×50 ml ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)

Sources & evidence

ORD record: ord-855537dd2e0a4c0f88bf6f83fb37b9f9
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04738972

Reaction notes

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