Sodium Hydroxide → HCID 58183705, compound

HRID 2043811Notes

Reaction equation

HRID 2043811 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([CH2:11][N:12]1[C:24]2[CH:23]=[CH:22][C:21]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[C:16]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:17]=2)=O.O.O1CCCC1.[OH-].[Na+]>O1CCCC1>[OH:8][CH2:9][CH2:11][N:12]1[C:24]2[CH:23]=[CH:22][C:21]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[C:16]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:17]=2

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 58183718HCID 58183718, compound

Product 1

HCID 58183705HCID 58183705, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension, cooled to 0° C., of 0.88 g (22.4 mmol) of 97% lithium aluminum hydride in 30 ml of tetrahydrofuran (THF) was added dropwise, under argon, a solution of 8.00 g (19.6 mmol) of N-methoxycarbonylmethyl-3,6-di-n-hexylcarbazole in 30 ml of THF within 15 min, in the course of which the temperature was kept at 0-5° C. The reaction mixture was allowed to warm to room temperature and stirred for a further 30 min. After the dropwise addition of 20 ml water/THF, the solution was stirred at room temperature for 15 min and then admixed with 2 ml of 10% NaOH, which precipitated a solid which was filtered off. The filtrate was admixed with 200 ml of diethyl ether/water (1:1). The aqueous phase was removed and extracted by shaking twice with 100 ml each time of diethyl ether. The combined organic phases were twice washed to neutrality with 100 ml of water each time and with 100 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated to dryness. 7.5 g (100% of theory) of colorless solid were obtained.

Workup

  1. additionwas added dropwise, under argon
  2. customwas kept at 0-5° C
  3. stirringthe solution was stirred at room temperature for 15 min
  4. customprecipitated a solid which
  5. filtrationwas filtered off
  6. customThe aqueous phase was removed
  7. extractionextracted
  8. stirringby shaking twice with 100 ml each time of diethyl ether
  9. washThe combined organic phases were twice washed
  10. dry with materialwith 100 ml of saturated sodium chloride solution, dried over sodium sulfate
  11. concentrationconcentrated to dryness
  12. custom7.5 g (100% of theory) of colorless solid were obtained

Sources & evidence

ORD record
ord-79b5209e97d84501a65968dc81a010c1
Source dataset
uspto-grants-2013_11
Patent number
US08586745B2

Reaction notes

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