Tetrahydrofuran → HCID 86699923, compound

HRID 530485Notes

Reaction equation

HRID 530485 reaction equation
O.[NH2:2][NH2:3].[OH-].[Na+].[CH3:6][CH2:7][O:8][C:9](C)=[O:10].[CH2:12]1[CH2:16][O:15][CH2:14][CH2:13]1>>[CH3:6][C:7]1([O:8][C:9](=[O:10])[NH:2][NH2:3])[CH2:13][CH2:14][O:15][CH2:16][CH2:12]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 86699923HCID 86699923, compound

Procedure

In a round bottomed flask equipped with a magnetic stirrer, crude (4-methyltetrahydropyran-4-yl)-(4-nitrophenyl)-carbonate from previous step (ca. 3.8 g) was dissolved in THF (50 mL), then hydrazine hydrate (1.97 mL, 40.57 mmol) was added in one portion. A yellow color immediately appeared which deepened to red in 1 h. After 3 h, 1.25M NaOH solution (50 mL) and AcOEt (50 mL) were added and the mixture stirred for 20 min. The phases were separated and the aqueous one washed with more AcOEt (25 mL). The combined organic liquors were washed with 1.25M NaOH solution (30 mL) (until clear colorless), dried over Na2SO4 and concentrated to leave a colorless oil (0.540 g, 24% over two steps) which was used in the next step without further purification. 1H NMR (CDCl3) δ 1.58 (s, 3H), 1.73 (m, 2H), 2.15 (m, 2H), 3.73 (m, 6H), 6.0 (bs, 1H).

Workup

  1. customIn a round bottomed flask equipped with a magnetic stirrer
  2. customred in 1 h
  3. customThe phases were separated
  4. washthe aqueous one washed with more AcOEt (25 mL)
  5. washThe combined organic liquors were washed with 1.25M NaOH solution (30 mL) (until clear colorless)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto leave a colorless oil (0.540 g, 24% over two steps) which
  9. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-92223f7978354b00b23b3e0360f32941
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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