Triethylamine → 202264-45-7

HRID 1844078Notes

Reaction equation

HRID 1844078 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=O)[CH:2]=[CH2:3].ClC(N(C)C)=C(C)C.C(N(CC)CC)C>ClCCl>[CH2:3]1[CH:2]2[CH2:1][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[CH:10]2[C:11]1=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 22590982HCID 22590982, compound

Product 1

HCID 4356718202264-45-7Yield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-allyl phenyl acetic acid (Example I2, Step 2, 0.095 g, 0.539 mmol) in dichloromethane (25 mL) was added at 0° C. 1-chloro-N,N,2-trimethyl-1-propenylamine (0.078 mL, 0.593 mmol). The solution was stirred for 1 h and then heated to reflux. Then, a solution of triethylamine (0.082 mL, 0.593 mmol) in dichloromethane (4 mL) was added slowly over two hours to the solution of the acid chloride at reflux. The reaction mixture was stirred for another 2 h and then cooled down. The solvents were removed in vacuo and the residue was purified by flash chromatography eluting with cyclohexane and ethyl acetate (20/1) to give 1,2a,7,7a-tetrahydro-2H-Cyclobut[a]inden-2-one (colourless oil, 56 mg, 66%) The analytical data were identical to the product obtained with the method A.

Workup

  1. customwas added at 0° C
  2. temperatureheated to reflux
  3. temperatureat reflux
  4. stirringThe reaction mixture was stirred for another 2 h
  5. temperaturecooled down
  6. customThe solvents were removed in vacuo
  7. customthe residue was purified by flash chromatography
  8. washeluting with cyclohexane and ethyl acetate (20/1)

Sources & evidence

ORD record
ord-a6f234076c4c4f8994a7f6dc5bb97a0d
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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