1,4-Dioxane → HCID 90312420, compound

HRID 1753660Notes

Reaction equation

HRID 1753660 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][CH2:10][N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:19]=2)[C:14]([CH3:29])=[CH:13][C:12]1([CH3:31])[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[O:34]1CCOCC1>CCOCC>[C:1]([O:5][C:6]([CH2:8][CH2:9][CH2:10][N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:19]=2)[C:14]([CH2:29][OH:34])=[CH:13][C:12]1([CH3:31])[CH3:30])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 4311764Sodium borohydrideHCID 90313418HCID 90313418, compound

Product 1

HCID 90312420HCID 90312420, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

SeO2 (1.50 g, 13.5 mmol) was added in portions to a hot (60° C.) solution of compound 4 (3.24 g, 6.74 mmol) in dioxane (50 mL). Then the reaction mixture was at this temperature for 1 h. After cooling, it was diluted with ether, and the organic layer was washed with sat. aq. NaHCO3 and dried over MgSO4. Solvents were evaporated, and the residue was purified by column chromatography (with hexane/ether/dichloromethane [10/3/1] as an eluent). After evaporation of solvents, the compound 5 (1.3 g) was dissolved in THF/MeOH (20/1), and NaBH4 (100 mg, 2.6 mmol) was added in portions at room temp. After 5 min, the reaction was complete (TLC). The excess of NaBH4 was destroyed by adding acetone (0.5 mL); all volatile materials were evaporated in vacuo, and the alcohol 6a was isolated by column chromatography (with hexane/ether/dichloromethane/MeOH mixture (10/3/4/0.3) as an eluent; Rf=0.42); yield 0.745 g (22%) of light yellow oil.

Workup

  1. temperatureAfter cooling
  2. washthe organic layer was washed with sat. aq. NaHCO3
  3. dry with materialdried over MgSO4
  4. customSolvents were evaporated
  5. customthe residue was purified by column chromatography (with hexane/ether/dichloromethane [10/3/1] as an eluent)
  6. customAfter evaporation of solvents
  7. dissolutionthe compound 5 (1.3 g) was dissolved in THF/MeOH (20/1)
  8. waitAfter 5 min
  9. customThe excess of NaBH4 was destroyed
  10. additionby adding acetone (0.5 mL)
  11. customall volatile materials were evaporated in vacuo

Sources & evidence

ORD record
ord-d1cdadab5fd0459fb32abd30cd3eeb79
Source dataset
uspto-grants-2015_10
Patent number
US09164086B2

Reaction notes

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