Water → HCID 22736389, compound

HRID 132123Notes

Reaction equation

HRID 132123 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.N1C=CC=CC=1.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:16].O>C(Cl)Cl>[C:15](=[O:16])([O:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[O:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 74956Tetrahydro-4H-pyran-4-olHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 22736389HCID 22736389, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tetrahydro-4H-pyran-4-ol (408 mg, 102 mmol) and pyridine (632 mg, 19.1 mmol) in 15 mL of CH2Cl2 was added p-nitrophenyl chloroformate (968 mg, 102 mmol). The mixture was stirred at rt for 30 h. Water was added and the organic layer was separated, and washed with 5% aq. citric acid. The organic layer was treated with an aq. solution of ammonia (NH4OH/H2O: ¼ v/v) for 15 min. The organic layer was separated, washed with aq. sodium bicarbonate and brine. After the solvent was removed, the desire product was isolated as a solid. 1H NMR (CD3Cl, 400 MHz) δ 1.80 (m, 2H), 2.00 (m, 2H), 3.52 (m, 2H), 3.92 (m, 2H), 4.88 (m, 1H), 7.32 (d, J=7 Hz, 2H), 8.21 (d, J=7 Hz, 2H).

Workup

  1. customthe organic layer was separated
  2. washwashed with 5% aq. citric acid
  3. additionThe organic layer was treated with an aq. solution of ammonia (NH4OH/H2O: ¼ v/v) for 15 min
  4. customThe organic layer was separated
  5. washwashed with aq. sodium bicarbonate and brine
  6. customAfter the solvent was removed
  7. customthe desire product was isolated as a solid

Sources & evidence

ORD record
ord-80a8e096ac3345b393df5fdd549b56cd
Source dataset
uspto-grants-2008_06
Patent number
US07384970B2

Reaction notes

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