Tetrahydrofuran → HCID 18779765, compound

HRID 1421758Notes

Reaction equation

HRID 1421758 reaction equation
ClC1C=CC(=O)N(C2C=CC(CC3N([CH2:20][C:21]4[CH:26]=[C:25]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:24]([C:33]#[N:34])=[CH:23][CH:22]=4)C=NC=3)=CN=2)C=1.[Li+].[BH4-].C1C[O:41]CC1>>[OH:41][CH2:20][C:21]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24]([C:33]#[N:34])=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 4148881Lithium borohydrideHCID 18779714HCID 18779714, compound

Product 1

HCID 18779765HCID 18779765, compound

Conditions

Temperature
70 °C

Procedure

6-Cyano-biphenyl-3-carboxylic acid methyl ester from step 2 (1.4 g, 5.9 mmol) was dissolved in THF (24 ml). LiBH4 in THF (2 M, 5.9 ml, 11.8 mmol) was added. The reaction mixture was heated to 70° C. for 3 hours. The reaction mixture was quenched carefully with 3N HCl and then extracted with EtOAc (3×20 mL). The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated to yield the desired product.

Workup

  1. customThe reaction mixture was quenched carefully with 3N HCl
  2. extractionextracted with EtOAc (3×20 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fcd2af2ec02e4bf5b3aea99cfb3d5916
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

Loading…