Sodium borohydride → 4-[2-(2-Hydroxyethyl)-2,3-dihydro-1-benzofuran-5-yl]benzonitrile

HRID 494816Notes

Reaction equation

HRID 494816 reaction equation
[O:1]=[CH:2][CH2:3][CH:4]1[CH2:8][C:7]2[CH:9]=[C:10]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[CH:11]=[CH:12][C:6]=2[O:5]1.[BH4-].[Na+]>CO>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:8][C:7]2[CH:9]=[C:10]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[CH:11]=[CH:12][C:6]=2[O:5]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 222744344-[2-(2-Oxoethyl)-2,3-dihydro-1-benzofuran-5-yl]benzonitrile

Product 1

HCID 222745974-[2-(2-Hydroxyethyl)-2,3-dihydro-1-benzofuran-5-yl]benzonitrileYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 67B (0.25 g, 0.95 mmol) and sodium borohydride (0.054 g, 1.42 mmol)in methanol (5 mL) was stirred for 1 hour, cooled on ice and quenched with aqueous NaHCO3 (50 mL). The mixture was extracted with dichloromethane (3×100 mL), the organic extracts combined and washed with water (1×150 mL), brine (1×150 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to provide the titled compound (0.24 g, 95%). 1HNMR (CDCl3): 1.90 (m, 2H), 2.90 (m, 2H), 3.46 (m, 2H), 5.40 (m, 1H), 6.85 (d, J=7 Hz, 1H), 7.38 (m, 2H), 7.65 (m, 4H); MS (DCI) 265 (M+), 283 (M+NH4+).

Workup

  1. temperaturecooled on ice
  2. customquenched with aqueous NaHCO3 (50 mL)
  3. extractionThe mixture was extracted with dichloromethane (3×100 mL)
  4. washwashed with water (1×150 mL), brine (1×150 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd4062b9f4de4606982d7d65cf6bdf6e
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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