Sodium Hydroxide → HCID 3159629, compound

HRID 920870Notes

Reaction equation

HRID 920870 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[O:14])=[CH:5]1)[CH:2]=[CH2:3].B1C2CCCC1CCC2.[OH-:24].[Na+]>C1COCC1.C(OCC)C>[OH:24][CH2:3][CH2:2][CH2:1][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[O:14])=[CH:5]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 8015161-Allyl-1H-indole-3-carbaldehyde

Product 1

HCID 3159629HCID 3159629, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a 10 mL round-bottom flask, 1-Allyl-1H-indole-3-carbaldehyde (169 mg, 0.91 mmol) is dissolved in 0.5 mL of anhydrous THF. To this solution is added 0.5 M of 9-BBN in THF (2 mL, 1.0 mmol). The reaction is allowed to stir at room temperature for 1 hr, whereupon a 1 M solution of NaOH (2.5 mL) is added. The organic layer is diluted with 10 mL of diethyl ether and the aqueous layer is removed. The organic layer is washed 3×10 mL with 1 M NaOH, followed by 2×10 mL water and 2×10 mL saturated NaCl solutions. The organic layer is then dried over Na2SO4 and the solvent is removed under reduced pressure to afford 1-(3-hydroxypropyl)-1H-indole-3-carbaldehyde.

Workup

  1. additionis added
  2. customthe aqueous layer is removed
  3. washThe organic layer is washed 3×10 mL with 1 M NaOH
  4. dry with materialThe organic layer is then dried over Na2SO4
  5. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-da8441dc81134df987d9391f489f8183
Source dataset
uspto-grants-2016_03
Patent number
US09273074B2

Reaction notes

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