Sodium hydride → HCID 66999940, compound

HRID 558145Notes

Reaction equation

HRID 558145 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[C:4]1=2.[C:19]([O:23][C:24](=[O:29])[NH:25][CH2:26][CH2:27]Br)([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C.C(Cl)(Cl)Cl.CC(O)C>[C:19]([O:23][C:24](=[O:29])[NH:25][CH2:26][CH2:27][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[C:4]2[S:3][CH:7]=[CH:6][C:5]=2[CH:8]=[CH:9][CH:10]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 57445096HCID 57445096, compound

Product 1

HCID 66999940HCID 66999940, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

Add sodium hydride (424 mg, 18 mmol) to a solution of 2-benzo[b]thiophen-7-yl-phenol (1 g, 4.4 mmol) in 10 mL of DMF. Stir the mixture at RT for 1 h and add (2-bromo-ethyl)-carbamic acid tert-butyl ester (2 g, 8.9 mmol). Continue to stir the reaction mixture for another 4 h at RT. Dilute the mixture with chloroform-IPA (3:1, 100 mL). Wash the organic phase with aqueous saturated sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo. Purify the residue by column chromatography (20% ethyl acetate in hexane) to give the title compound as a pale yellow solid (1.4 g, 86%). MS (ES) m/z 392 [M+Na]+.

Workup

  1. stirringContinue to stir the reaction mixture for another 4 h at RT
  2. washWash the organic phase with aqueous saturated sodium chloride and water
  3. dry with materialDry the mixture over sodium sulfate
  4. concentrationConcentrate the solution in vacuo
  5. customPurify the residue by column chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ce555aa8bdc246eba34d24230fbd9e3e
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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