Potassium Carbonate → HCID 67374631, compound

HRID 1805904Notes

Reaction equation

HRID 1805904 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][O:19][P:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[CH:13][CH:12]=1)(=O)C>CO>[P:20]([O:19][CH2:18][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([OH:10])=[CH:12][CH:13]=1)([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67374285HCID 67374285, compound

Product 1

HCID 67374631HCID 67374631, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Potassium carbonate (62.8 mg, 0.454 mmol) was added to a stirred solution of 4-(2-{[bis(benzyloxy)phosphoryl]oxy}ethyl)phenyl acetate (100 mg, 0.227 mmol) in MeOH (20.5 mL) at 25° C. The reaction was stirred at 25° C. for 1 h. The reaction mixture was concentrated in vacuo and the resulting residue was partitioned between water (20 mL) and EtOAc (20 mL). The aqueous layer was separated and extracted with EtOAc (2×20 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to afford dibenzyl 2-(4-hydroxyphenyl)ethyl phosphate, as an oil. LCMS calc.=399.1; found=398.9 (M+H)+. 1H NMR (500 MHz, CHCl3): δ 8.05 (1 H, s); 7.41-7.30 (m, 10 H); 6.99 (d, J=8.2 Hz, 2 H); 6.86 (d, J=8.3 Hz, 2 H); 5.02 (s, 2 H); 5.00 (s, 2 H); 4.18 (q, J=7.1 Hz, 2 H); 2.86 (t, J=7.1 Hz, 2 H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue was partitioned between water (20 mL) and EtOAc (20 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc (2×20 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf5efbb13435408ab88222afa410784e
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

Loading…