Dichloromethane → HCID 14280461, compound

HRID 1763054Notes

Reaction equation

HRID 1763054 reaction equation
[OH:1][CH:2]([CH:9]([CH3:13])[CH2:10][CH2:11][CH3:12])[CH:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C(Cl)Cl>O1CCCC1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH3:8][CH:3]([CH:2]([O:1][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][O:14]1)[CH:9]([CH3:13])[CH2:10][CH2:11][CH3:12])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyranHCID 14280459HCID 14280459, compound

Product 1

HCID 14280461HCID 14280461, compoundYield 121.2%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)Catalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

200 mg (1.06 mmol) of methyl (+)-3-hydroxy-2,4-dimethylheptanoate (+)-(4) was dissolved in 4 ml of tetrahydrofuran, and 134 mg (1.59 mmol) of dihydropyran and 1 mg of pyridinium p-toluenesulfonate were added, and the mixture was reacted overnight at room temperature. Since TLC (Thin Layer Chromatography) showed that the starting materials still remained, 5 mg of pyridinium p-toluenesulfonate and 3 ml of methylene chloride were added, and the reaction was further carried out overnight at room temperature. The reaction mixture was extracted with ether. The ethereal layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and then with an aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, filtered, and concentrated to give 350 mg of crude methyl (+)-2,4-dimethyl-3-tetrahydropyranyloxy-1-heptanoate.

Workup

  1. customthe mixture was reacted overnight at room temperature
  2. extractionThe reaction mixture was extracted with ether
  3. washThe ethereal layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialwith an aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2c77f05425714e6eba63d689e7136ab7
Source dataset
uspto-grants-1989_05
Patent number
US04835292

Reaction notes

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