Water → 2-(6-Cyano-2-octynyloxy)tetrahydropyran

HRID 2351797Notes

Reaction equation

HRID 2351797 reaction equation
Cl[CH:2]([CH2:15][CH3:16])[CH2:3][CH2:4][C:5]#[C:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1.[C-:17]#[N:18].[Na+].O>CS(C)=O>[C:17]([CH:2]([CH2:15][CH3:16])[CH2:3][CH2:4][C:5]#[C:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)#[N:18]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 148379472-(6-Chloro-2-octynyloxy)tetrahydropyran

Product 1

HCID 148379482-(6-Cyano-2-octynyloxy)tetrahydropyranYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of chloride 35 (20.0 g, 92.3 mmol) in dry DMSO (75 mL) was added to a solution of NaCN (6.0 g, 122.0 mmol) in dry DMSO (100 mL). The reaction mixture was stirred at 50°-60° C. for 65 h. The dark brown mixture was cooled, poured into water (200 mL), and extracted with five 100-mL portions of CH2Cl2. The combined organic extracts were washed with water (3×150 mL), dried over Na2SO4, and concentrated by rotary evaporation. The black oil was dissolved in Et2O (200 mL) and filtered through a pad of silica gel (60-200 mesh, Baker Chemical Co.) to yield 36 as a yellow oil (14.3 g, 75%): IR (neat) 2940 (s), 2870, 2280 (w), 2250, 1440, 1345, 1200, 1130, 1115 (s), 1075, 1020 (s), 900, 865, 810 cm-1 ; 1H NMR (CDCl3)δ 4.80 (m, 1H), 4.23 (t, J=2 Hz, 2H), 3.66 (m, 2H), (m, 4H), 1.67 (m, 8H). Nitrile 36 was used without further purification.

Workup

  1. temperatureThe dark brown mixture was cooled
  2. extractionextracted with five 100-mL portions of CH2Cl2
  3. washThe combined organic extracts were washed with water (3×150 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by rotary evaporation
  6. dissolutionThe black oil was dissolved in Et2O (200 mL)
  7. filtrationfiltered through a pad of silica gel (60-200 mesh, Baker Chemical Co.)

Sources & evidence

ORD record
ord-a98586f5cf814aa09e1cb37e547488f5
Source dataset
uspto-grants-1989_10
Patent number
US04873360

Reaction notes

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