Dimethyl Sulfoxide → HCID 66887075, compound

HRID 75193Notes

Reaction equation

HRID 75193 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH2:13][O:14][CH:15]=[CH2:16])[CH2:9][CH2:8]1)(=O)=O.CS(C)=O.[C-:21]#[N:22].[Na+]>>[CH:15]([O:14][CH2:13][CH:10]1[CH2:11][CH2:12][CH:7]([CH2:6][C:21]#[N:22])[CH2:8][CH2:9]1)=[CH2:16]

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 86613264HCID 86613264, compound

Product 1

HCID 66887075HCID 66887075, compoundYield 87.2%

Conditions

Temperature
25 °C

Procedure

4-[(Vinyloxy)methyl]cyclohexylmethyl methanesulfonate (1.43 g, 0.00576 mol) was dissolved in dimethyl sulfoxide (5 mL, 0.07 mol), and then sodium cyanide (1 g, 0.02 mol) was added. The reaction was stirred at 60° C. for 2 hours at 25° C. for 16 hours. The reaction was extracted with ethyl acetate and the extracts were washed with water, brine 3×, and then dried over MgSO4 and concentrated in vacuo. The product was purified via column chromatography on silica gel (20% ethyl acetate, 80% hexanes) to give 0.90 g of the desired product as a mixture of the two diastereomers. 1H NMR (400 MHz, CDCl3): δ 6.33-6.48 (m, 1 H), 4.96-4.13 (m, 1H), 4.00-3.96 (m, 1H), 3.49-3.50 (m, 2H), 2.26 (d, 2H, J=6.8 Hz), 1.86-1.93 (m, 4H), 1.56-1.70 (m, 3H), 1.41-1.52 (m, 1H), 0.95-1.20 (m, 4H). (major isomer).

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. washthe extracts were washed with water, brine 3×
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe product was purified via column chromatography on silica gel (20% ethyl acetate, 80% hexanes)

Sources & evidence

ORD record
ord-d1d657b4be0c4753807af6cafd0b13b5
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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