3,4-dihydro-2H-pyran → HCID 118021717, compound

HRID 575683Notes

Reaction equation

HRID 575683 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:10]([CH2:13][CH2:14][OH:15])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CC(=O)OCC>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([S:10]([CH2:13][CH2:14][O:15][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][O:16]2)(=[O:11])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 8857Ethyl AcetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 116852751HCID 116852751, compound

Product 1

HCID 118021717HCID 118021717, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the title compound of step 3 (1.0 g, 3.4 mmol) in CH2Cl2 (10 mL) was added 3,4-dihydro-2H-pyran (1.4 g, 17.0 mmol) followed by pyridinium p-toluensulfonate (64.6 mg, 0.34 mmol). After stirring at r.t. 12 h, the mixture was subjected to CH2Cl2 extractive work up & silica gel chromatography (PE:EA=1:0˜5:1) to give the title compound (1.1 g, 85.6%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 8.11 (d, J=2.4 Hz, 1H), 7.86 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.00 (d, J=8.8 Hz, 1H), 4.51 (dd, J1=4.0 Hz, J2=2.4 Hz, 1H), 4.09-4.03 (m, 1H), 3.98 (s, 3H), 3.84-3.79 (m, 1H), 3.79-3.74 (m, 1H), 3.50-3.46 (m, 1H), 3.45-3.42 (m, 2H), 1.58-1.37 (m, 6H). LCMS: 401.0, 403.0 (M+Na)+.

Workup

  1. custom12 h

Sources & evidence

ORD record
ord-9f8ea6b9431b4678862483ea73bd36f6
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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