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

HRID 2050163Notes

Reaction equation

HRID 2050163 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 (5.36 g; 6.02 mole) in dry DMF (30 ml) was treated with 100% sodium hydride (0.48 g; 0.02 mole) and stirred at 100° for about 1 hr. To this was added a solution of 1-(4-Acetyl-3-hydroxy-2-n-propylphenoxy)-3-chloro-2-propanol (7 g) in DMF (2 ml) and the mixture stirred at 100° for an additional 4 hrs. After removal of the solvent in vacuo, water was added and the product extracted into chloroform. Chromatography of the extract on 300 g of silica gel eluting with chloroform afforded the title compound as a white crystalline solid of Rf 0.38. mp (EtOH) 172°-173°. Yield 4.38 g (42%). νmax (mull) 1715; 1630; 1620 cm-1. (DMSO) 9.19 (3H, t, J 7.0 Hz); 8.58 (2H, sextuplet, J. 7.0 Hz); 7.48 (3H, S+ 2 H 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 9 Hz); 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 4 hrs
  2. customAfter removal of the solvent in vacuo, water
  3. additionwas added
  4. extractionthe product extracted into chloroform
  5. extractionChromatography of the extract on 300 g of silica gel eluting with chloroform

Sources & evidence

ORD record
ord-1a18f25096b64cf79226b3695ef9478d
Source dataset
uspto-grants-1980_04
Patent number
US04200577

Reaction notes

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