3,4-dihydro-2H-pyran → 1-(t-Butyldimethylsilanyloxy)-3-chloro-2-(tetrahydropyran-2-yloxy)propane

HRID 1092882Notes

Reaction equation

HRID 1092882 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([OH:13])[CH2:11][Cl:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Si:1]([O:8][CH2:9][CH:10]([O:13][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][O:14]1)[CH2:11][Cl:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86604379(R)-(-)-1-(tert-butyldimethylsilanyloxy)-3-chloropropan-2-ol

Product 1

HCID 230802371-(t-Butyldimethylsilanyloxy)-3-chloro-2-(tetrahydropyran-2-yloxy)propaneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-(−)-1-(tert-Butyldimethylsilanyloxy)-3-chloropropan-2-ol (11.19 g) prepared in reference example 31 was dissolved in dichloromethane (20 ml), then 3,4-dihydro-2H-pyran (5.87 ml) and pyridinium p-toluenesulfonate (catalytic amount) were added, then the reaction mixture was stirred at a room temperature overnight. The reaction mixture was concentrated under a reduced pressure, the residue was purified by use of a silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1), there was obtained 1-(t-butyldimethylsilanyloxy)-3-chloro-2-(tetrahydropyran-2-yloxy)propane (14.14 g, yield: 92.0%) as colorless liquid product.

Workup

  1. concentrationThe reaction mixture was concentrated under a reduced pressure
  2. customthe residue was purified by use of a silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-dd8e2739f23b42ff91b8935d2ff055d1
Source dataset
uspto-grants-2012_03
Patent number
US08129544B2

Reaction notes

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