Dichloromethane → HCID 56633974, compound

HRID 638625Notes

Reaction equation

HRID 638625 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[C@H:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][C@H:11]1[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1.C(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C.N1C=CC=CC=1>[CH2:1]([O:8][CH2:9][C@@H:10]1[C@H:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][C@H:11]1[O:20][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 56624700HCID 56624700, compound

Product 1

HCID 56633974HCID 56633974, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 8.52 g of (1R,2S,3S)-2-benzyloxymethyl-3-methoxycarbonylmethylcyclopentan-1-ol (prepared in Reference Example 2), 7.4 ml of 2,3-dihydropyran and 30 ml of methylene chloride was prepared and then cooled. To the mixture 370 mg of p-toluenesulphonic acid monohydrate was added, the mixture was stirred for 20 min. at 0° C., and for 30 min. at room temperature. After addition of 1 ml of pyridine, the mixture was diluted with 300 ml of diethyl ether. The diluted solution was washed with water, dilute hydrochloric acid, an aqueous solution of sodium bicarbonate and water successively, dried over anhydrous magnesium sulphate and concentrated under reduced pressure to give 14.2 g of the title compound having the following physical characteristics.

Workup

  1. customwas prepared
  2. temperaturecooled
  3. waitfor 30 min. at room temperature
  4. washThe diluted solution was washed with water, dilute hydrochloric acid
  5. dry with materialan aqueous solution of sodium bicarbonate and water successively, dried over anhydrous magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7377525e57f41b58a51d55a87d45a41
Source dataset
uspto-grants-1985_12
Patent number
US04562207

Reaction notes

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