Iodoethane → HCID 67264596, compound

HRID 1688156Notes

Reaction equation

HRID 1688156 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:19]=[CH:18][C:11]2[CH2:12][CH2:13][O:14][C:15](=[O:17])[NH:16][C:10]=2[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:27][CH3:28]>CN(C=O)C.O>[C:1]([O:5][C:6]([C:8]1[CH:19]=[CH:18][C:11]2[CH2:12][CH2:13][O:14][C:15](=[O:17])[N:16]([CH2:27][CH3:28])[C:10]=2[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 57853898HCID 57853898, compound

Product 1

HCID 67264596HCID 67264596, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-oxo-5,6,8,9-tetrahydro-7-oxa-5-aza-benzocycloheptene-3-carboxylic acid tert-butyl ester (1.1 g, 4.18 mmol), potassium carbonate (2.5 g, 18.1 mmol, 4.3 eq.) and iodoethane (1.67 mL, 20.87 mmol, 5 eq.) was stirred in DMF (20 mL) for 16 hours at 60° C. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried (sodium sulfate) and concentrated. Silica gel chromatography (0→20% ethyl acetate in hexanes) provided 5-ethyl-6-oxo-5,6,8,9-tetrahydro-7-oxa-5-aza-benzocycloheptene-3-carboxylic acid tert-butyl ester as pale solid in quantitative yield: 1H NMR (400 MHz, CDCl3) δ 7.81 (s, 1H), 7.80 (dd, 1H), 7.28 (d, 1H), 4.48 (t, 2H), 3.91 (q, 2H), 3.00 (t, 2H), 1.59 (s, 9H), 1.23 (t, 3H).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined organic layers were dried (sodium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bdb11e7ce5ad4f07b45dc5755d6ae88d
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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