3,4-dihydro-2H-pyran → HCID 21075359, compound

HRID 1373757Notes

Reaction equation

HRID 1373757 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1>ClCCl.CC1C=CC(S(O)(=O)=O)=CC=1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][O:21]2)=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 13846344HCID 13846344, compound

Product 1

HCID 21075359HCID 21075359, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 69B (0.89 g, 3.27 mmol), 3,4-dihydro-2H-pyran (1.49 mL, 16.34 mmol) and p-TsOH.H2O (5 mg) in dichloromethane (20 mL) were stirred at room temperature overnight. The reaction solution was dried with silica gel powder (15 g). 20% ethyl acetate in hexanes (1 L) was used to run flash chromatography to give the title compound (1.06 g, 91%). MS (DCI) m/z 375.13 (M+NH4)+; 1H NMR (400 MHz, CDCl3) δ ppm 1.42–1.62 (m, 4 H) 1.68 (m, 1 H) 1.79 (m, 1 H) 2.88 (t, J=6.60 Hz, 2 H) 3.45 (m, 1 H) 3.59 (m, 1 H) 3.70 (m, 1 H) 3.94 (m, 1 H) 4.58 (t, J=3.38 Hz, 1 H) 5.21 (s, 2 H) 7.03 (d, J=8.59 Hz, 1 H) 7.28–7.48 (m, 6 H) 7.77 (d, J=2.15 Hz, 1 H).

Workup

  1. customThe reaction solution was dried with silica gel powder (15 g)

Sources & evidence

ORD record
ord-6ede2f7505544a71a353267c9ce81a7d
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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