Potassium Carbonate → Dibenzyl 2-(4-hydroxy-3-methoxyphenyl)ethyl phosphate

HRID 1805931Notes

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][C:12]=1[O:38][CH3:39])(=O)C>CO>[P:20]([O:19][CH2:18][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([OH:10])=[C:12]([O:38][CH3:39])[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:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21]

Participants

Conditions

Temperature: 25 °C

Procedure

K2CO3 (126 mg, 0.910 mmol) was added to a stirred solution of 4-(2-{[bis(benzyloxy)phosphoryl]oxy}ethyl)-2-methoxyphenyl acetate (214 mg, 0.455 mmol) in MeOH (30 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-hydroxy-3-methoxyphenyl)ethyl phosphate, as an oil. LCMS calc.=429.2; found=429.1 (M±Na)+.

Workup

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

Sources & evidence

ORD record: ord-f1290ffc3a2045e182215440dc76a744
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354454B2

Reaction notes

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