Cyclohexanol → HCID 59557761, compound

HRID 2038470Notes

Reaction equation

HRID 2038470 reaction equation
[CH:1]1(O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CC1C=CC(S([O:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]3[CH:36]=[C:35]([Br:37])[CH:34]=[CH:33][C:32]=3[Cl:38])=[CH:26][CH:25]=2)(=O)=O)=CC=1>C1COCC1>[Br:37][C:35]1[CH:34]=[CH:33][C:32]([Cl:38])=[C:31]([CH2:30][C:27]2[CH:26]=[CH:25][C:24]([O:23][CH2:22][CH2:21][O:20][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:29][CH:28]=2)[CH:36]=1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 595577472-(4-(5-Bromo-2-chlorobenzyl)phenoxy)ethyl 4-methylbenzenesulfonate

Product 1

HCID 59557761HCID 59557761, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of cyclohexanol (0.76 g, 7.56 mmol) in anhydrous THF (10 mL), NaH (60%, 0.18 g, 7.56 mmol) was added in portions at 0° C. The mixture was stirred at 0° C. for 0.5 h, and then 2-(4-(5-bromo-2-chlorobenzyl)phenoxy)ethyl 4-methylbenzenesulfonate (intermediate AB) (0.66 g, 1.26 mmol) was added in portions. Then the mixture was stirred at room temperature overnight, whereupon TLC showed the reaction was complete. Then the reaction mixture was quenched with saturated NH4Cl, extracted with EtOAc, washed with water and brine, dried with anhydrous Na2SO4, and concentrated to a crude oil. The crude oil was purified by column chromatography (PE:EA=100:1) to obtain oil AE (0.3 g, yield 56.6%). 1H NMR (400 MHz, CD3OD): δ 7.28-7.21 (m, 3H), 7.07 (d, 2H, J=8.8 Hz), 6.86 (d, 2H, J=8.4 Hz), 4.08 (t, 2H, J=4.8 Hz), 3.98 (s, 2H), 3.80 (t, 2H, J=4.8 Hz), 3.40-3.20 (m, 1H), 1.95-1.93 (m, 2H), 1.76-1.73 (m, 2H), 1.32-1.22 (m, 6H).

Workup

  1. stirringThen the mixture was stirred at room temperature overnight, whereupon TLC
  2. customThen the reaction mixture was quenched with saturated NH4Cl
  3. extractionextracted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried with anhydrous Na2SO4
  6. concentrationconcentrated to a crude oil
  7. customThe crude oil was purified by column chromatography (PE:EA=100:1)
  8. customto obtain oil AE (0.3 g, yield 56.6%)

Sources & evidence

ORD record
ord-02869771346b4c7a8e281a31a2f9fd54
Source dataset
uspto-grants-2013_11
Patent number
US08575321B2

Reaction notes

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