p-Toluenesulfonic acid → 3-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile

HRID 2267041Notes

Reaction equation

HRID 2267041 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18].[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C(=O)(O)[O-].[Na+]>ClCCl>[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 27346773-(Hydroxymethyl)benzonitrile

Product 1

HCID 219279093-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add p-toluene sulphonic acid (2.11 g, 12.2 mmol) to a solution of 3-hydroxymethyl-benzonitrile (16.30 g, 122.4 mmol) and 3,4-dihydro-2H-pyran (51.5 g, 612 mmol) in dicliloromethane (500 ml) and stir. After 90 minutes, pour reaction into saturated sodium bicarbonate, remove organics, dry with sodium sulfate, filter and concentrate to give a dark brown oil. Purify the residue by flash chromatography eluting with a gradient of 10-15% ethyl acetate:hexanes to yield the title product as a clear oil (16.20 g, 61%): 1H NMR (CDCl3) δ 1.53-1.91 (m, 6H), 3.56 (m, 1H), 3.88 (m, 1H), 4.53 (d, 1H), 4.72 (t, 1H), 4.81 (d, 1H), 7.45 (t, 1H), 7.58 (m, 2H), 7.69 (s, 1H)

Workup

  1. additionpour
  2. customremove organics
  3. dry with materialdry with sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto give a dark brown oil
  7. customPurify the residue by flash chromatography
  8. washeluting with a gradient of 10-15% ethyl acetate

Sources & evidence

ORD record
ord-46b89cf9506b49638fb46451a89b75f0
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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