HCID 68941078, compound → HCID 68941603, compound

HRID 900986Notes

Reaction equation

HRID 900986 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([C:10](O)=[O:11])[S:7][C:8]=1[CH3:9])#[N:2]>C1COCC1>[OH:11][CH2:10][C:6]1[S:7][C:8]([CH3:9])=[C:4]([CH2:3][C:1]#[N:2])[CH:5]=1

Participants

3

Reactant 1

HCID 68941078HCID 68941078, compound

Product 1

HCID 68941603HCID 68941603, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-cyanomethyl-5-methyl-thiophene-2-carboxylic acid (12.3g, 67.9 mmol) in THF (400 mL) is treated with borane-dimethylsulfide complex (7.5 mL, 10 M, 74.7 mmol) dropwise via syringe. The mixture is heated to a gentle reflux for 2 h. After cooling, the mixture is quenched with water and extracted with dichloromethane (3×). The combined organic layers are dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue is purified by flash chromatography (silica gel, 30-50% ethyl acetate in heptane) to give (5-hydroxymethyl-2-methyl-thiophen-3-yl)-acetonitrile (4.7 g, 41.4%) as a white solid. mp 66-68° C.; 1H NMR (CDCl3, 300 MHz) δ 6.83 (s, 1 H), 4.71 (d, J=6.0 Hz, 2 H), 3.56 (s, 2 H), 2.40 (s, 3 H), 1.75 (t, J=6.0 Hz, 1 H).

Workup

  1. temperatureThe mixture is heated to
  2. temperaturea gentle reflux for 2 h
  3. temperatureAfter cooling
  4. customthe mixture is quenched with water
  5. extractionextracted with dichloromethane (3×)
  6. dry with materialThe combined organic layers are dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue is purified by flash chromatography (silica gel, 30-50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6f76d616ddee4b1db41b0fc108ab5c9f
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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