Sodium hydride → 7-(3-[4-Acetyl-3-hydroxy-2-n-propylphenoxy]-2-hydroxypropoxy)-4-benzyloxycoumarin

HRID 2163714Notes

Reaction equation

HRID 2163714 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:23]([C:26]1[CH:37]=[CH:36][C:29]([O:30][CH2:31][CH:32]([OH:35])[CH2:33]Cl)=[C:28]([CH2:38][CH2:39][CH3:40])[C:27]=1[OH:41])(=[O:25])[CH3:24]>CN(C=O)C>[C:23]([C:26]1[CH:37]=[CH:36][C:29]([O:30][CH2:31][CH:32]([OH:35])[CH2:33][O:19][C:15]2[CH:14]=[C:13]3[C:18]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:10][C:11](=[O:20])[O:12]3)=[CH:17][CH:16]=2)=[C:28]([CH2:38][CH2:39][CH3:40])[C:27]=1[OH:41])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 134084074-Benzyloxy-7-hydroxycoumarinHCID 203314601-(4Acetyl-3-hydroxy-2-n-propylphenoxy)-3-chloro-2-propanol

Product 1

HCID 203314247-(3-[4-Acetyl-3-hydroxy-2-n-propylphenoxy]-2-hydroxypropoxy)-4-benzyloxycoumarin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-benzyloxy-7-hydroxycoumarin (5.36g; 6.02 mole) in dry DMF (30 ml) was treated with 100% sodium hydride (0.48g; 0.02 mole) and stirred at 100° for about 1 hr. To this was added a solution of 1-(4Acetyl-3-hydroxy-2-n-propylphenoxy)-3-chloro-2-propanol (7g) in DMF (2ml) and the mixture stirred at 100° for an additional 4hrs. After removal of the solvent in vacuo, water was added and the product extracted into chloroform. Chromatography of the extract on 300g of silica gel eluting with chloroform afforded the title compound as a white crystalline solid of Rf 0.38. mp (EtOH) 172°-173°. Yield 4.38g (42%). νmax (mull) 1715; 1630; 1620 cm-1. (DMSO) 9.19 (3H, t, J 7.0Hz); 8.58 (2H, sextuplet, J. 7.0Hz); 7.48 (3H, S + 2H m); 6.71 (1H sharp exchangeable); 5.80 (5H, S); 4.68 (2H, S), 4.50 (1H, broad exchangeable); 4.13 (1H, S); 3.32 (1H, d, J 9Hz); 3.12-2.15 (12H, m); 1 low field sharp exchangeable. (Found; C, 69.30; H, 5.80; C30H30O8 requires; C 69.49; H, 5.83%).

Workup

  1. stirringthe mixture stirred at 100° for an additional 4hrs
  2. customAfter removal of the solvent in vacuo, water
  3. additionwas added
  4. extractionthe product extracted into chloroform
  5. extractionChromatography of the extract on 300g of silica gel eluting with chloroform

Sources & evidence

ORD record
ord-f21f32da1ca34c6da5b40b7aebc0180e
Source dataset
uspto-grants-1979_01
Patent number
US04136192

Reaction notes

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