Methanol → HCID 70981943, compound

HRID 2280696Notes

Reaction equation

HRID 2280696 reaction equation
[Si:1]([O:8][CH:9]1[O:14][CH2:13][CH:12]([OH:15])[CH:11]=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:16](OC(=O)C)(=[O:18])[CH3:17].CO.O>C(Cl)Cl>[C:16]([O:15][CH:12]1[CH:11]=[CH:10][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[O:14][CH2:13]1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 7918Acetic AnhydrideHCID 70981112HCID 70981112, compound

Product 1

HCID 70981943HCID 70981943, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-ol (13.3 g, 57.7 mmol) and TEA (16.09 mL, 115 mmol) in DCM (200 mL) was added acetic anhydride (27.2 mL, 289 mmol), and the mixture was stirred at room temperature overnight. Methanol (˜3 mL) was added and the mixture was stirred for 30 min at room temperature before adding water and transferring to a separatory funnel. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and condensed. The crude material was purified on a 340G SNAP Biotage column (0-50% ethyl acetate in hexane) to give 6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-yl acetate (13.6 g, 49.9 mmol, 86% yield) as a pale yellow oil; 1H NMR (400 MHz, CDCl3) δ ppm 5.84-5.88 (m, 2H), 5.26-5.28 (m, 1H), 5.20-5.25 (m, 1H), 3.84 (dd, J=6.25, 1.95 Hz, 2H), 2.08 (s, 3H), 0.91 (s, 9H), 0.13 (d, J=1.17 Hz, 6H).

Workup

  1. stirringthe mixture was stirred for 30 min at room temperature
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customcondensed
  6. customThe crude material was purified on a 340G SNAP Biotage column (0-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-08b4ee2803424e1db2ac898df50505d4
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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