3-Methyl-2-cyclohexen-1-one → (2R,3R)-7-methyl-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-6-ene

HRID 715488

Reaction equation

HRID 715488 reaction equation
[C:1]1([C@@H:7]([OH:16])[C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][C:18]1[CH2:23][CH2:22][CH2:21][C:20](=O)[CH:19]=1>C1C=CC=CC=1.CCOCC.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>[CH3:17][C:18]1[CH2:23][CH2:22][CH2:21][C:20]2([O:9][C@H:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:16]2)[CH:19]=1

Participants

6

Reactant 2

HCID 145113-Methyl-2-cyclohexen-1-oneHCID 853019(R,R)-Hydrobenzoin

Product 1

HCID 71116085(2R,3R)-7-methyl-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-6-eneYield 100%

Reagents, catalysts & solvents 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
115 °C

Procedure

(1R,2R)-1,2-diphenyl-1,2-ethanediol (150 g, 699 mmol) and 3-methyl-2-cyclohexen-1-one (77 g, 699 mmol) were suspended in benzene (1398 mL) and treated with PPTS (4.39 g, 17.48 mmol). The flask was fitted with a Dean-Stark trap filled with benzene and a condenser. The reaction was heated to 115° C. for 3 days, and then the reaction was cooled to ambient temperature and diluted with ether. The mixture was washed with saturated aq NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated to give a red/orange liquid (214 g, 100% yield). The liquid was used without further purification.

Workup

  1. customThe flask was fitted with a Dean-Stark trap
  2. temperaturethe reaction was cooled to ambient temperature
  3. washThe mixture was washed with saturated aq NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e2fd549a67fb4e3d9ed1a4dad0240270
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Linked notes

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