Ethanol → HCID 178473089, compound

HRID 646468Notes

Reaction equation

HRID 646468 reaction equation
[Na].C(O)C.[CH2:5]([O:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([Cl:27])=[CH:15][C:14]=1[C:28](=[O:30])[CH3:29])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:31](OCC)(=[O:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33]>C(O)(=O)C>[CH2:35]([O:34][C:32](=[O:33])[C:31]([OH:37])=[CH:29][C:28]([C:14]1[CH:15]=[C:16]([Cl:27])[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:18][C:13]=1[O:12][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:30])[CH3:36]

Participants

6

Reactant 4

HCID 702EthanolHCID 7268Diethyl OxalateHCID 5360545Sodium2×HCID 179636911-(2,4-Bis(benzyloxy)-5-chlorophenyl)ethanone

Product 1

HCID 178473089HCID 178473089, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium metal (1.35 g, 0.058 mol) was added in small pieces over a period of 20 minutes to stirred anhydrous ethanol under a nitrogen atmosphere. The reaction mixture was then stirred for a further 10 minutes until all the sodium had reacted to give a homogeneous solution. 1-(2,4-bis-benzyloxy-5-chloro-phenyl)-ethanone (10.0 g, 0.027 mol) was added in portions over 2-3 minutes and the resulting suspension was stirred for 5 minutes prior to addition of diethyl oxalate (6 ml, 0.043 mol) which afforded a thicker, yellow precipitate. The reaction mixture was heated to reflux (giving homogeneous brown solution) for 4 hours, then allowed to cool to room temperature and acetic acid (6 ml) was added. The resulting which solid forms was triturated, filtered, washed with ethanol and dried to give a yellow solid (12.0 g, 95%). 1H NMR (400 MHz, CDCl3) δ 1.2 (t, 3H), 4.19 (q, 2H), 5.05 (s, 2H), 5.10 (s, 2H), 6.50 (s, 1H), 7.22-7.41 (m, 10H), 7.97 (s, 1H).

Workup

  1. customhad reacted
  2. customto give a homogeneous solution
  3. customafforded a thicker, yellow precipitate
  4. temperatureThe reaction mixture was heated
  5. temperatureto reflux
  6. custom(giving homogeneous brown solution) for 4 hours
  7. customThe resulting which solid forms was triturated
  8. filtrationfiltered
  9. washwashed with ethanol
  10. customdried

Sources & evidence

ORD record
ord-c0353d1772604a0ca634435d4c71ff0a
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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