Acetic Anhydride → HCID 15507553, compound

HRID 520397Notes

Reaction equation

HRID 520397 reaction equation
[CH2:1]([O:8]OC1COC(O)CC1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)[CH:20]([CH3:22])[CH3:21].[C:26]([O:29][C:30](=[O:32])[CH3:31])(=[O:28])[CH3:27]>C(Cl)Cl>[C:26]([O:29][CH:30]1[CH2:31][CH2:22][CH:20]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:21][O:32]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 86690106HCID 86690106, compound

Product 1

HCID 15507553HCID 15507553, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(benzyloxy)-2-methoxytetrahydro-2H-pyran (317 mg, 1.426 mmol) in AcOH (10 mL) and water (5 mL) was heated at 55° C. for 12 h and then evaporated to dryness to afford 5-benzyloxyoxytetrahydropyran-2-ol (300 mg). 5-Benzyloxyoxytetrahydropyran-2-ol was dissolved in DCM (3 mL) and treated with DIPEA (0.374 mL, 2.139 mmol) and acetic anhydride (218 mg, 2.139 mmol). The mixture was stirred at rt for 4 h, quenched with sat. NaHCO3 and extracted with DCM. The organic phase was washed with water, brine, dried (MgSO4) and concentrated to yield 5-(benzyloxy)tetrahydro-2H-pyran-2-yl acetate as a clear oil (281 mg).

Workup

  1. customquenched with sat. NaHCO3
  2. extractionextracted with DCM
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-82d8f9ed33b6420594e06ffe538c573f
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

Loading…