Dimethyl Sulfoxide → HCID 86747150, compound

HRID 2255128Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]([Si:15]([CH3:35])([CH3:34])[O:16][C:17]1[CH:22]=[C:21]([CH2:23][OH:24])[CH:20]=[CH:19][C:18]=1[CH2:25][P:26](=[O:33])([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])([CH3:14])[CH3:13].C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:12]([Si:15]([CH3:35])([CH3:34])[O:16][C:17]1[CH:22]=[C:21]([CH:23]=[O:24])[CH:20]=[CH:19][C:18]=1[CH2:25][P:26](=[O:33])([O:27][CH2:28][CH3:29])[O:30][CH2:31][CH3:32])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of oxalylchloride (0.6 g, 6.7 mmol) in 20 mL methylene chloride is cooled to -70° C. Dimethylsulfoxide (0.6 mL, 8.4 mmol) is added dropwise. The solution is warmed to -30° C. then cooled to -70° C. A solution of diethyl [[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(hydroxymethyl)phenyl]methyl]phosphonate (1.73 g, 4.45 mmol) from Preparation 18 in methylenechloride (15 mL) is added to the reaction mixture. The reaction mixture is stirred for 0.5 hours then warmed to -35° C. Triethylamine (4.7 mL, 33.5 mmol) is added and the mixture allowed to warm to room temperature. Methylenechloride (400 mL) is added and the organic phase is washed with 100 mL H2O. The organic phase is dried (MgSO4) and concentrated. The residue is passed through a 200-g silica gel plug using 5% MeOH/CH2Cl2 as the eluent. An oil of diethyl [[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-formylphenyl]methyl]phosphonate is obtained (1.67 g, 97%).

Workup

temperaturethen cooled to -70° C
additionis added to the reaction mixture
temperaturethen warmed to -35° C
temperatureto warm to room temperature
washthe organic phase is washed with 100 mL H2O
dry with materialThe organic phase is dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-851ffe9835304e2d85e3a9edf838ba71
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05238958

Reaction notes

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