Methanesulfonic Acid → 4-(3,6-dihydro-2H-pyran-4-yl)benzonitrile

HRID 1961438Notes

Reaction equation

HRID 1961438 reaction equation
CS(O)(=O)=O.O[C:7]1([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[BH4-].[Na+].[OH-].[Na+]>C(Cl)Cl>[O:10]1[CH2:9][CH:8]=[C:7]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 595046634-(4-Hydroxytetrahydro-2H-pyran-4-yl)benzenecarbonitrile

Product 1

HCID 666330234-(3,6-dihydro-2H-pyran-4-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

12.65 ml (195 mmol) MeSO3H in 10 ml CH2Cl2 was slowly added to a mixture of 611 mg (3.0 mmol) 4-(4-hydroxytetrahydro-2H-pyran-4-yl)benzonitrile and 1.13 g (30 mmol) NaBH4 in 15 ml CH2Cl2 at 0° C. Stirred for 1 h. 2M NaOH was added until pH>10. The mixture was extracted with CH2Cl2. The organic phase was dried (MgSO4) and concentrated. The crude product (450 mg, 81%) was used directly in the next step.

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-71a78143f7674dfc95cc65c37a91402f
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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