3,4-dihydro-2H-pyran → HCID 90303368, compound

HRID 1051923Notes

Reaction equation

HRID 1051923 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH:11]([C:13]1[S:17][C:16]([Cl:18])=[N:15][C:14]=1[Cl:19])[OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH2:10][CH:11]([C:13]1[S:17][C:16]([Cl:18])=[N:15][C:14]=1[Cl:19])[O:12][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][O:20]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 90303294HCID 90303294, compound

Product 1

HCID 90303368HCID 90303368, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A soln. of 3-((tert-butyldimethylsilyl)oxy)-1-(2,4-dichlorothiazol-5-yl)propan-1-ol (6.62 g, 19.3 mmol), 3,4-dihydro-2H-pyran (8.9 mL, 96.7 mmol) and PPTS (0.49 g, 1.93 mmol) in DCM (75 mL) was stirred under reflux for 2 h. Subsequently, the volatiles were removed in vacuo and the residue was purified by means of CC (1-10% EtOAc/Hept) to provide the product as colorless oil as an isomeric mixture.

Workup

  1. temperatureunder reflux for 2 h
  2. customSubsequently, the volatiles were removed in vacuo
  3. customthe residue was purified by means of CC (1-10% EtOAc/Hept)

Sources & evidence

ORD record
ord-0e190790ea814b988933aa9b280738bb
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

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