Water → HCID 45083778, compound

HRID 900995Notes

Reaction equation

HRID 900995 reaction equation
[C:1]([CH2:3][C:4]1[S:8][CH:7]=[C:6]([C:9](O)=[O:10])[CH:5]=1)#[N:2].CSC.B.O>C1COCC1>[OH:10][CH2:9][C:6]1[CH:5]=[C:4]([CH2:3][C:1]#[N:2])[S:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12423031(Dimethyl sulfide)trihydroboronHCID 59698789HCID 59698789, compound

Product 1

HCID 45083778HCID 45083778, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-cyanomethyl-thiophene-3-carboxylic acid (2.7 g, 16.1 mmol) in THF (95 mL) is treated with borane dimethylsulfide (1.78 mL, 10.0 M, 17.8 mmol) in a dropwise maner. After the addition is complete, the solution is warmed to reflux for 1 h. After cooling, water is added and the mixture is extracted with dichloromethane (3×). The combined extracts are dried over Na2SO4, filtered and concentrated in vacuo. The residue is purified by flash chromatography (silica gel, 30-50% ethyl acetate in heptane) to give (4-hydroxymethyl-thiophen-2-yl)-acetonitrile (1.7 g, 69%) as a white solid: mp 45-47° C.; 1H NMR (CDCl3, 300 MHz) δ 7.16 (s, 1 H), 7.02 (s, 1 H), 4.60 (s, 2 H), 3.84 (s, 2 H), 1.79 (s, 1 H).

Workup

  1. additionAfter the addition
  2. temperaturethe solution is warmed
  3. temperatureto reflux for 1 h
  4. temperatureAfter cooling
  5. extractionthe mixture is extracted with dichloromethane (3×)
  6. dry with materialThe combined extracts are dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by flash chromatography (silica gel, 30-50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b7e39d2e94664d028fcefa12ce3fa2b9
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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