Cyclohexanol → HCID 67523662, compound

HRID 2190937Notes

Reaction equation

HRID 2190937 reaction equation
[OH:1][C:2]1[C:7]2[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:15]1(O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH:15]1([O:1][C:2]2[C:7]3[C:8](=[O:14])[O:9][C:10]([CH3:12])([CH3:13])[O:11][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 110525144H-1,3-Benzodioxin-4-one, 5-hydroxy-2,2-dimethyl-

Product 1

HCID 67523662HCID 67523662, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cold mixture of 5-hydroxy-2,2-dimethyl-benzo[1,3]dioxin-4-one (1 g, 5.21 mmol) and cyclohexanol (1.98 g, 19.8 mmol) and triphenyl phosphine (2.46 g, 9.38 mmol) in THF in an ice bath was added diisopropyl azodicarboxylate (DIAD) (1.94 g, 9.59 mmol). Resulting mixture was stirred at 0° C. for 15 min and then at rt for 1 h. Reaction mixture was concentrated and the residue was purified by silica gel chromatography (eluting with 50%-100% CH2Cl2 in hexanes) to provide the title compound (0.97 g). 1H NMR (200 MHz, CDCl3): δ (ppm)=7.36 (t, J=8.2 Hz, 1H), 6.60 (d, J=8.6 Hz, 1H), 6.47 (d, J=8.2 Hz, 1H), 4.39 (m, 1H), 1.93-1.37 (m, 10H), 1.69 (s, 6H).

Workup

  1. customResulting mixture
  2. waitat rt for 1 h
  3. customReaction mixture
  4. concentrationwas concentrated
  5. customthe residue was purified by silica gel chromatography (eluting with 50%-100% CH2Cl2 in hexanes)

Sources & evidence

ORD record
ord-c7df3c2b56524ff29da4630353b2a810
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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