Dimethylformamide → HCID 15341838, compound

HRID 893475Notes

Reaction equation

HRID 893475 reaction equation
[CH:1]1([CH2:4][C:5]2[C:6]([OH:16])=[C:7]([CH:12]=[CH:13][C:14]=2[OH:15])[C:8]([NH:10][CH3:11])=[O:9])[CH2:3][CH2:2]1.I[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:38]=[CH:37][C:25]2[CH2:26][CH2:27][CH:28]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[O:29][C:24]=2[C:23]=1[CH2:39][CH2:40][CH3:41].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C.CCCCCC.O>[CH:1]1([CH2:4][C:5]2[C:6]([OH:16])=[C:7]([C:8]([NH:10][CH3:11])=[O:9])[CH:12]=[CH:13][C:14]=2[O:15][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:38]=[CH:37][C:25]3[CH2:26][CH2:27][CH:28]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[O:29][C:24]=3[C:23]=2[CH2:39][CH2:40][CH3:41])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 15341794HCID 15341794, compoundHCID 153418003-(Cyclopropylmethyl)-2,4-dihydroxy-N-methylbenzamide

Product 1

HCID 15341838HCID 15341838, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The compound of Example 16 (340 mg, 1.53 mmol), ethyl 3,4-dihydro-7-(3-iodopropoxy)-8-propyl-2H-I-benzopyran-2propanoate (685 mg, 1.53 mmol), and potassium carbonate (276 mg, 2.00 mmol) were added to 2.0 ml of DMF, and the reaction mixture was stirred at room temperature overnight. Water (50 ml) was added to the reaction mixture and it was extracted four times with 30 ml aliquots of ethyl acetate. The combined ethyl acetate extracts were washed with water, then dried over magnesium sulfate, filtered and concentrated in vacuo to give a brown oil. Chromatography of the oil on silica gel with 30/70 ethyl acetate/hexane as eluant gave the product as a white solid (200 mg).

Workup

  1. extractionwas extracted four times with 30 ml aliquots of ethyl acetate
  2. washThe combined ethyl acetate extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil

Sources & evidence

ORD record
ord-2051d1ebae29408aac813d31e5c3710d
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

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