3,4-dihydro-2H-pyran → HCID 88322193, compound

HRID 861847Notes

Reaction equation

HRID 861847 reaction equation
[CH2:1]([C:3]([OH:20])([C:6]#[C:7][CH2:8][O:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:4][CH3:5])[CH3:2].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[O:38]1[CH:43]=[CH:42][CH2:41][CH2:40][CH2:39]1>ClCCl>[CH2:1]([C:3]([O:20][CH:39]1[CH2:40][CH2:41][CH2:42][CH2:43][O:38]1)([CH2:4][CH3:5])[C:6]#[C:7][CH2:8][O:9][S:10]([C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1)(=[O:12])=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 19700523HCID 19700523, compound

Product 1

HCID 88322193HCID 88322193, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Compound 401 (6.5 g), PPTS (0.73 g) and 3,4-dihydro-2H-pyran (2 g) in dichloromethane (33 ml) was stirred at r.t. for 17 h. Dichloromethane (250 ml) was added and the solution was washed with brine (250 ml). Work-up with chromatography with ether/pentane 1:1 (v/v) gave the title compound (7.1 g). 1H NMR: 0.85 (t, 6H), 1.55 (q, 4H), 1.42-1.90 (m, 6H), 2.45 (s, 3H), 3.47 (m, 1H), 3.89 (m, 1H), 4.79 (s, 2H), 4.85 (m, 1H), 7.35 (d, 2H), 7.82 (d, 2H) .

Workup

  1. washthe solution was washed with brine (250 ml)

Sources & evidence

ORD record
ord-102aa9248c454746a4875ef0a64a1ff9
Source dataset
uspto-grants-1998_02
Patent number
US05716945

Reaction notes

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