HCID 5702750, compound → HCID 23506679, compound

HRID 1883523Notes

Reaction equation

HRID 1883523 reaction equation
[CH2:1]([CH:5]([C:12]1[C:13](=[O:23])[O:14][C:15]2[C:20]([C:21]=1[OH:22])=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:2]([CH3:4])=[O:3].[C:24](Cl)(=[O:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]/[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>O1CCOCC1.N1C=CC=CC=1>[CH2:1]([CH:5]([C:12]1[C:13](=[O:23])[O:14][C:15]2[C:20]([C:21]=1[O:22][C:24](=[O:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]/[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 2

HCID 5702750HCID 5702750, compoundHCID 54678486Warfarin

Product 1

HCID 23506679HCID 23506679, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(α-acetonylbenzyl)-4-hydroxycoumarin (warfarin) (3.70 g, 12 mmol) in 120 ml anhydrous dioxane and 25 ml pyridine was added elaidic acid chloride (3.60 g, 12 mmol) and the reaction mixture was stirred at ambient temperature for 4 hours. The solvents were evaporated at high vacuum. The residue was partitioned between ether and water. The organic phase was washed with tartaric acid (aq), NaHCO3 (aq) and water. The dried organic phase was concentrated and the product purified on a column of slica gel with heptane/ethylacetate (6:1) as the eluent system. Impure fractions were repurified and homogenous fractions were evaporated to give 5.1 g (70%) of the title compound as a pale yellow oil.

Workup

  1. customThe solvents were evaporated at high vacuum
  2. customThe residue was partitioned between ether and water
  3. washThe organic phase was washed with tartaric acid (aq), NaHCO3 (aq) and water
  4. concentrationThe dried organic phase was concentrated
  5. customthe product purified on a column of slica gel with heptane/ethylacetate (6:1) as the eluent system
  6. customImpure fractions were repurified
  7. customhomogenous fractions were evaporated

Sources & evidence

ORD record
ord-5cc335b549dd41bd8161a38b9c6bff88
Source dataset
uspto-grants-2004_07
Patent number
US06762175B2

Reaction notes

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