Sodium Chloride → 4-Tetrahydropyranyloxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one

HRID 2420444Notes

Reaction equation

HRID 2420444 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1.[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl-].[Na+].C(=O)(O)[O-].[Na+]>CCOCC.CO.C(Cl)Cl>[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 98379417-(3-Hydroxy-5-oxo-1-cyclopentenyl)-heptanoic acid ethyl ester

Product 1

HCID 131895154-Tetrahydropyranyloxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 674 mg. (2.64 mmoles) of 4-hydroxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one (Example 1302) and 2.22 g. (26.4 mmoles) of dihydropyran in 2.6 ml. of methylene chloride is added 5.0 mg. (0.026 mmoles) of p-toluenesulfonic acid monohydrate. After stirring for 20 minutes at room temperature the solution is diluted with ether and poured into saturated sodium chloride solution containing a little sodium bicarbonate. The organic phase is separated and washed with saturated sodium chloride solution. The extract is dried over magnesium sulfate, and volatile matter is evaporated at reduced pressure to give an oil, λmax.MeOH = 224 mμ (7950); max. = 1735 (ester carbonyl group), 1710 (ketone carbonyl group), and 1030 cm-1 (tetrahydropyranyloxy group).

Workup

  1. customThe organic phase is separated
  2. washwashed with saturated sodium chloride solution
  3. dry with materialThe extract is dried over magnesium sulfate, and volatile matter
  4. customis evaporated at reduced pressure
  5. customto give an oil, λmax

Sources & evidence

ORD record
ord-2194c01043144a54b70a25c4b20bfd50
Source dataset
uspto-grants-1978_08
Patent number
US04110368

Reaction notes

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