Methanol → HCID 19982294, compound

HRID 982079Notes

Reaction equation

OOS([O-])=O.[K+].[C:7]1([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[NH:15][N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:30]=[CH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]C.C[OH:42]>ClCCl>[C:7]1([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:15]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[O:42])[N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Oxone was bubbled through a solution of 3,4,5-triphenyl-lH-pyrazole-1-undecene (6.78 g, 15 mmol) in dichloromethane (175 mL) and methanol (0.73 g, 22 mmol) maintained at -78° C. for 1.5 hours. The ozone supply was removed, dimethylsulfide (30 mL) added and the mixture allowed to warm to room temperature over 2 hours. The solution was dried over sodium sulfate, concentrated in vacuo and the residue chromatographed on a column of silica gel. Elution with a mixture of hexane and ethyl acetate (9:1) gave 3,4,5-triphenyl-lH-pyrazole-1-decanal (2.93 g, 43%) as an oil. MS(CI): m/e =451 (MH+).

Workup

customThe ozone supply was removed
additiondimethylsulfide (30 mL) added
temperatureto warm to room temperature over 2 hours
dry with materialThe solution was dried over sodium sulfate
concentrationconcentrated in vacuo
customthe residue chromatographed on a column of silica gel
washElution
additionwith a mixture of hexane and ethyl acetate (9:1)

Sources & evidence

ORD record: ord-a457c9712fd64c68aa2c8a8448c947b5
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994482

Reaction notes

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