Diethyl Ether → HCID 10444152, compound

HRID 1420702Notes

Reaction equation

HRID 1420702 reaction equation
[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[Br:18][CH2:19][C@@H:20]([CH3:23])[CH2:21][OH:22].[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1.C(OCC)C>C(Cl)Cl>[Br:18][CH2:19][C@@H:20]([CH3:23])[CH2:21][O:22][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][O:24]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 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, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium-4-toluenesulfonate (PPTs) (0.18g, 0.072 mmol) was dissolved in dry CH2Cl2 (30 mL), (S)-(+)-3-bromo-2-methyl-1-propanol (1.1 g, 7.2 mmol) and 2,3-dihydro-4H-pyran (DHP) (0.60 g, 7.2 mmol) were added. The mixture was stirred under a N2 atmosphere at room temperature for 5 h. Diethylether (20 mL) was added and the resulting mixture was washed with brine (820 mL), dried (MgSO4) and the solvents were removed In vacuo. This afforded a crude product which on ball-tube-distillation (90° C./0.1 mmHg) gave the title compound 1.07 g (63%).

Workup

  1. washthe resulting mixture was washed with brine (820 mL)
  2. dry with materialdried (MgSO4)
  3. customthe solvents were removed In vacuo
  4. customThis afforded a crude product which
  5. distillationon ball-tube-distillation (90° C./0.1 mmHg)

Sources & evidence

ORD record
ord-a77d4b2d97774047a5f51162d07b1790
Source dataset
uspto-grants-2000_06
Patent number
US06071932

Reaction notes

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