Cyclohexanol → HCID 22989979, compound

HRID 1169342Notes

Reaction equation

HRID 1169342 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:20]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.O[C:28]1[CH:29]=[CH:30][C:31]2[CH2:37][CH2:36][CH2:35][C:34]([C:38]([O:40][CH3:41])=[O:39])=[CH:33][C:32]=2[CH:42]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH:20]1([O:26][C:28]2[CH:29]=[CH:30][C:31]3[CH2:37][CH2:36][CH2:35][C:34]([C:38]([O:40][CH3:41])=[O:39])=[CH:33][C:32]=3[CH:42]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 22989944methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

Product 1

HCID 22989979HCID 22989979, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To triphenylphosphine (1.18 g, 4.50 mmol), cyclohexanol (0.468 ml, 4.50 mmol) and methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (327 mg, 1.50 mmol) dissolved in THF (6 ml) was added at 0° C. a solution of diisopropyl azodicarboxylate (0.886 ml, 4.50 mmol) in THF (4 ml), and the resulting mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure and the residue was subjected to column chromatography (silica gel: 45 g, ethyl acetate/hexane=1/25). The objective fractions were concentrated under reduced pressure to obtain methyl 2-cyclohexyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (434 mg, 1.44 mmol, 96%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationThe objective fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-565c5d9c6d1e404e8a41ec071b3476fd
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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