Tetrahydrofuran → HCID 58873068, compound

HRID 1990102Notes

Reaction equation

[C:1]([O:4][CH2:5][CH2:6]Br)(=[O:3])[CH3:2].[Li].[C:9]([C:13]1[CH:28]=[CH:27][C:16]([C:17]([C:19](=[C:22](SC)[S:23][CH3:24])[C:20]#[N:21])=O)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].[Cl-].[NH4+].C1C[O:34]CC1>CCOC(C)=O>[CH2:5]([O:4][C:1]([C:2]1[O:34][C:22]([S:23][CH3:24])=[C:19]([C:20]#[N:21])[C:17]=1[C:16]1[CH:27]=[CH:28][C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:14][CH:15]=1)=[O:3])[CH3:6]

Participants

Conditions

Temperature: -78 °C

Procedure

Add a solution of the bromoethyl acetate (2.13 ml, 19.17 mmol) in THF (10 ml) dropwise to a −78 ° C. solution of the lithium hexamethylsillylamide (1M, 21 ml, 20.7 mmol) in THF. Stir the mixture at −78° C. for 10 minutes and treat with a dropwise solution of 2-(4-tert-butyl-benzoyl)-3,3-bis-methylsulfanyl-acrylonitrile (2.25 g, 7.67 mmol) in THF (20 ml). Stir the mixture at −78° C. for 30 minutes and at RT for 6 h. Pour into a saturated solution of ammonium chloride (100 ml). Extract organic with EtOAc (3×100 ml). Combine the organics wash with water (3×100 ml), brine (100 ml), dry over magnesium sulfate, filter and concentrate under reduced pressure. Purification by flash chromatography, eluting with ethyl acetate:hexanes (1:9) provides the title compound (1 g, 38%): Mass spectrum (M+1)=344.

Workup

stirringStir the mixture at −78° C. for 30 minutes
waitat RT for 6 h
washCombine the organics wash with water (3×100 ml), brine (100 ml)
dry with materialdry over magnesium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customPurification by flash chromatography
washeluting with ethyl acetate:hexanes (1:9)

Sources & evidence

ORD record: ord-685cedf2830b4efcada1d290e6f9dcda
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642361B2

Reaction notes

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