Tetrahydrofuran → HCID 86699920, compound

HRID 530482Notes

Reaction equation

HRID 530482 reaction equation
[OH2:1].[NH2:2][NH2:3].[OH-].[Na+].[CH3:6][C:7]([O:10][CH3:11])([CH3:9])[CH3:8].[CH2:12]1[CH2:16]OC[CH2:13]1>>[CH3:6][C:7]1([O:10][C:11](=[O:1])[NH:2][NH2:3])[CH2:9][CH2:16][CH2:12][CH2:13][CH2:8]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 86699920HCID 86699920, compoundYield 98%

Procedure

In a round bottomed flask equipped with a magnetic stirrer (1-methylcyclohexyl)-(4-nitrophenyl)-carbonate (0.816 g, 2.92 mmol) was dissolved in THF (7 mL) and after 5 min hydrazine hydrate (0.28 mL, 5.85 mmol) was added in one portion. A yellow color immediately appeared which deepened to red in 1 hr. After 3 hr at rt, 1.25M NaOH solution (20 mL) and MTBE (25 mL) were added and the mixture was stirred for 10 min. The two phases were separated and the organic phase was washed again with 1.25M NaOH solution (15 mL) for 10 min (until colorless solution), dried over Na2SO4 and concentrated to give a colorless oil (0.497 g, 98%), which is used in the next step without purification. 1H NMR (CDCl3): δ 1.20-1.60 (m, 8H), 1.49 (s, 3H), 2.10 (m, 2H), 3.67 (bs, 2H), 5.81 (bs, 1H).

Workup

  1. additionwas added in one portion
  2. customred in 1 hr
  3. customThe two phases were separated
  4. washthe organic phase was washed again with 1.25M NaOH solution (15 mL) for 10 min (until colorless solution)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d02ccdc028bb4fb28b409031276b9893
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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