Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 54408141, compound

HRID 365045Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][CH:9]=[CH:10][C:11]2[CH:27]=[CH:26][C:14]([C:15]([N:17]([CH3:25])[O:18]C3CCCCO3)=[O:16])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO.CCOCC>[OH:18][N:17]([CH3:25])[C:15](=[O:16])[C:14]1[CH:13]=[CH:12][C:11]([CH:10]=[CH:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 4-(4-phenyl-1-butenyl)-N-methyl-N-(tetrahydropyran-2-yloxy)benzamide (prepared in Example 1 Part E) (500 mg, 1.37 mmol) in 12 ml of CH3OH under argon was added pyridinium 4-toluenesulfonate (344 mg, 1.0 eq.). The mixture was heated to 55° C. and stirred for 2.5 hours. The solution was diluted with ether and washed with 1/2 saturate sodium chloride (20 ml) and brine (10 ml). The organic layer was dried over anhydrous MgSO4 and reduced to yield a light yellow oil which was flash chromatographed on Merck silica gel, eluting with (7:3) Hex:EtOAc. Product containing fractions were concentrated in vacuo to yield title product, 426 mg (85%) as a golden oil.

Workup

washwashed with 1/2
concentrationsaturate sodium chloride (20 ml) and brine (10 ml)
dry with materialThe organic layer was dried over anhydrous MgSO4
customto yield a light yellow oil which
customchromatographed on Merck silica gel
washeluting with (7:3) Hex
additionProduct containing fractions
concentrationwere concentrated in vacuo

Sources & evidence

ORD record: ord-eca60640149f4d0babdc6993e118606b
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04607053

Reaction notes

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