Water → HCID 178495005, compound

HRID 713930Notes

Reaction equation

HRID 713930 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]([OH:17])([CH3:16])[CH3:15])[CH2:10][CH2:9]1.[H-].[Na+].[CH3:20]I.O>C1COCC1>[CH3:20][O:17][C:14]([C@H:11]1[CH2:12][CH2:13][C@H:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH2:9][CH2:10]1)([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178459278HCID 178459278, compound

Product 1

HCID 178495005HCID 178495005, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-((trans)-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl)propan-2-ol (1.56 g, 6.5 mmol) in THF (10 mL) was added NaH (300 mg, 13 mmol, 2.0 eq) slowly at r.t. and then CH3I (1.96 g, 13 mmol, 2.0 eq) was added in one portion. The mixture was stirred at 50° C. for 2 h, Water (10 mL) was added and the mixture was extracted with EA (30 mL×3), dried and concentrated to give the title compound as a colorless oil (1.2 g, yield: 72%). 1H NMR (400 MHz, CDCl3) δ: 4.64 (t, 1H), 3.93-3.89 (m, 2H), 3.51-3.47 (m, 1H), 3.17 (s, 3H), 1.97-1.85 (m, 3H), 1.70-1.67 (m, 1H), 1.58-1.43 (m, 9H), 1.34-1.27 (m, 2H), 1.09 (d, 6H).

Workup

  1. extractionthe mixture was extracted with EA (30 mL×3)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-db0e1933a112477ab20d8f1d7935ec03
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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