Triethylamine → Methyl 3-((3-oxo-4,5,6,7-tetrahydroisobenzofuran-1(3h)-ylidene)methyl)benzoate

HRID 1259293Notes

Reaction equation

HRID 1259293 reaction equation
[Br-].C([P+](CCCC)(CCCC)[CH:7]1[C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=2[C:9](=[O:16])[O:8]1)CCC.[CH3:25][O:26][C:27](=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]=O)[CH:29]=1.C(N(CC)CC)C>ClCCl>[O:16]=[C:9]1[C:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:7](=[CH:34][C:30]2[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=2)[C:27]([O:26][CH3:25])=[O:36])[O:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 639145Methyl 3-formylbenzoateHCID 66966753Tributyl(3-oxo-1,3,4,5,6,7-hexahydro-2-benzofuran-1-yl)phosphonium bromide

Product 1

HCID 69044378Methyl 3-((3-oxo-4,5,6,7-tetrahydroisobenzofuran-1(3h)-ylidene)methyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 1B (25.8 g, 61.5 mmol), methyl-3-formylbenzoate (10.01 g, 61.0 mmol), and triethylamine (8.7 mL, 62.4 mmol) in dichloromethane (125 mL) was stirred at room temperature for 16 hours, and concentrated. The residue was stirred with a mixture of ethyl acetate and water. The precipitated solid was filtered, washed with water, and dried to provide the title compound. MS (DCI/NH3) m/z 285 (M+H)+.

Workup

  1. concentrationconcentrated
  2. filtrationThe precipitated solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-bcfbbbc5c34f46a48aebf2cb6e68f1c5
Source dataset
uspto-grants-2013_06
Patent number
US08466150B2

Reaction notes

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