Diethyl Ether → HCID 67899298, compound

HRID 345230Notes

Reaction equation

HRID 345230 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([OH:19])[C@@:11]([O:17][CH3:18])([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CCOCC>ClCCl>[CH2:1]([O:8][CH2:9][C@@H:10]([O:19][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][O:20]1)[C@@:11]([O:17][CH3:18])([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 14213436HCID 14213436, compound

Product 1

HCID 67899298HCID 67899298, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2R,3R)l-benzyloxy-3-methoxy-3-methyl-6-heptene-2-ol (10) (37.1 mmol, 9.8 g), dihydropyran (55.7 mmol, 5.1 ml) and pyridinium paratoluene sulfonate (3.71 mmol, 0.93 g) in anhydrous dichloromethane (100 ml) is stirred under nitrogen atmosphere for 24 h. Ether (400 ml) is added, and the organic layer is washed with water, brine, saturated aqueous NaHCO3 and brine. After drying over anhydrous magnesium sulfate the solvent is flash evaporated. The product 11b is used as such in the next reaction.

Workup

  1. washthe organic layer is washed with water, brine, saturated aqueous NaHCO3 and brine
  2. dry with materialAfter drying over anhydrous magnesium sulfate the solvent
  3. customevaporated
  4. customsuch in the next reaction

Sources & evidence

ORD record
ord-01713f7bf3e4463fb774765ecd4a6677
Source dataset
uspto-grants-1991_10
Patent number
US05055592

Reaction notes

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