Dimethyl Sulfoxide → 2-(4-Formylcyclohexyl)acetonitrile

HRID 75195Notes

Reaction equation

HRID 75195 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][C:20]#[N:21])[CH2:15][CH2:14]1.C(N(CC)CC)C.[Na+].[Cl-]>ClCCl>[CH:12]([CH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][C:20]#[N:21])[CH2:15][CH2:14]1)=[O:11]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66886391HCID 66886391, compound

Product 1

HCID 866132652-(4-Formylcyclohexyl)acetonitrileYield 80.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of oxalyl chloride (0.24 mL, 0.0028 mol) in dichloromethane (15 mL) at −78° C. was added a solution of dimethyl sulfoxide (0.23 mL, 0.0032 mol) in dichloromethane (5 mL). After 10 min. a solution of [4-(hydroxymethyl)cyclohexyl]acetonitrile (0.38 g, 0.0025 mol) in dichloromethane (2 mL) was added to the reaction mixture. After 25 min., the reaction mixture was treated with triethylamine (1.7 mL, 0.012 mol), allowed to warm to room temperature, and then poured into 100 mL of saturated aqueous NaCl. The resulting mixture was extracted with two 100 mL portions of ether, dried (MgSO4), and then evaporated under reduced pressure. Chromatography of the residue on silica gel with 1:10 ethyl acetate/hexanes afforded 0.306 g of the desired product. 1H NMR (300 MHz, CDCl3): δ 9.64 (s, 1H), 2.35 (d, 2H J=10.8 Hz) 1.10-2.4 (m, 10 H) (major isomer).

Workup

  1. extractionThe resulting mixture was extracted with two 100 mL portions of ether
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1fe6748c50bc4b0697fa5590b97fe52e
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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