Hydrochloric Acid → HCID 54515668, compound

HRID 2255127Notes

Reaction equation

HRID 2255127 reaction equation
[CH3:1][C:2]([Si:5]([CH3:32])([CH3:31])[O:6][C:7]1[CH:12]=[C:11]([CH2:13][O:14][Si](C(C)(C)C)(C)C)[CH:10]=[CH:9][C:8]=1[CH2:22][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])([CH3:4])[CH3:3].Cl.CCOC(C)=O.O>C(O)C>[CH3:1][C:2]([Si:5]([CH3:32])([CH3:31])[O:6][C:7]1[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][C:8]=1[CH2:22][P:23](=[O:30])([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 53777773HCID 53777773, compound

Product 1

HCID 54515668HCID 54515668, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diethyl [[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]phenyl]methyl]phosphonate (3.23 g, 6.4 mmol) from Preparation 17 in ethanol (30 mL) at 0° C. is treated with 1 mL of 1N HCl. The mixture is stirred at 0° C. for 2 hours. The solution is poured onto 500 mL EtOAc and water (50 mL). The organic phase is separated, dried (MgSO4), and concentrated. The residue is purified by silica gel chromatography (2.5% MeOH/CH2Cl2 followed by 5% MeOH/CH2Cl2). A colorless oil of diethyl [[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(hydroxymethyl)phenyl]methyl]phosphonate is obtained (1.73 g, 69%).

Workup

  1. customThe organic phase is separated
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is purified by silica gel chromatography (2.5% MeOH/CH2Cl2 followed by 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3c21eeaffb234bd483f70185d9a982fc
Source dataset
uspto-grants-1993_08
Patent number
US05238958

Reaction notes

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