Ethanol → HCID 20161193, compound

HRID 247016Notes

Reaction equation

HRID 247016 reaction equation
[C:1]([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:14][CH3:15])=[C:8]([O:12][CH3:13])[CH:9]=2)[C:4]1=O)#[N:2].[BH4-].[Na+].ClCCl.C([OH:24])C>O>[OH:24][C:3]1([C:1]#[N:2])[CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:14][CH3:15])=[C:8]([O:12][CH3:13])[CH:9]=2)[CH2:4]1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 201611865,6-Dimethoxy-1-oxo-2,3-dihydro-1H-indene-2-carbonitrile

Product 1

HCID 20161193HCID 20161193, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Cyano-5,6-dimethoxy-indan-1-one (18.2 g) was suspended in ethanol (360 ml) under an atmosphere of nitrogen and treated with a solution of sodium borohydride (6.57 g) in water (25 ml) and ethanol (36 ml). After 11/2 hours dichloromethane (200 ml) was added. After a further 30 minutes the excess sodium borohydride was destroyed by the dropwise addition of acetic acid (2 ml) in dichloromethane (10 ml). The inorganic salts were filtered off and the filtrate was concentrated under reduced pressure then extracted into ethyl acetate (3×200 ml). The organic extracts were combined, washed with brine, dried over magnesium sulphate, filtered and evaporated to dryness to give 2-hydroxy-5,6-dimethoxyindane-2-carbonitrile as a yellow solid (17.1 g).

Workup

  1. customAfter a further 30 minutes the excess sodium borohydride was destroyed by the dropwise addition of acetic acid (2 ml) in dichloromethane (10 ml)
  2. filtrationThe inorganic salts were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. extractionthen extracted into ethyl acetate (3×200 ml)
  5. washwashed with brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-0213fc743e164588a5b1c6a81203f9b3
Source dataset
uspto-grants-1987_11
Patent number
US04705782

Reaction notes

Loading…