3,4-dihydro-2H-pyran → HCID 10444152, compound

HRID 2064532Notes

Reaction equation

HRID 2064532 reaction equation
[Br:1][CH2:2][C@@H:3]([CH3:6])[CH2:4][OH:5].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Br:1][CH2:2][C@@H:3]([CH3:6])[CH2:4][O:5][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10986449(S)-(+)-3-Bromo-2-methyl-1-propanol

Product 1

HCID 10444152HCID 10444152, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-3-bromo-2-methylpropan-1-ol (7.30 g, 5 mL, 47.7 mmol) in anhydrous dichloromethane (100 mL) was mixed with 3,4-dihydro-2H-pyrane (4.63 g, 5.02 mL, 55 mmol) and pyridinium tosylate (50 mg) with ice cooling and then stirred for 1 h at room temperature. The reaction mixture was then washed with 5% sodium hydrogencarbonate solution and water (3×30 mL each). The combined organic phases were dried with sodium sulphate and concentrated to low volume in a vacuum.

Workup

  1. washThe reaction mixture was then washed with 5% sodium hydrogencarbonate solution and water (3×30 mL each)
  2. dry with materialThe combined organic phases were dried with sodium sulphate
  3. concentrationconcentrated to low volume in a vacuum

Sources & evidence

ORD record
ord-da0f3f4f506b47a6bee23c8c534768c9
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

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