Methyl formate → HCID 22561313, compound

HRID 983667Notes

Reaction equation

HRID 983667 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]#[N:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[CH:27](OC)=[O:28]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:27]=[O:28])[C:16]3[C:11](=[CH:12][C:13]([C:17]#[N:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 2724682Lithium diisopropylamideHCID 98561591-(4'-Fluorophenyl)-1,3-DihydroIsobenzofuran-5-Carbonitrile

Product 1

HCID 22561313HCID 22561313, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of 1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile (2.4 g, 10 mmol) in THF (15 mL) was added to a solution of LDA (11 mmol) in THF (25 mL) at −78° C. under an atmosphere of nitrogen. The mixture was allowed to warm to −40° C. during 45 min. Freshly distilled methyl formate (0.75 mL, 12 mmol) was added at this temperature, and stirring was continued for 1 h while warming to 0° C. Then the mixture was poured into ice/saturated ammonium chloride solution, and extracted with Et2O (3×100 mL). The organic extracts were washed with brine, dried and evaporated. Silica gel chromatography (heptane, EtOAc 4:1) of the residue gave the product (1.3 g, 50%). 1H NMR (CDCl3) δ 5.35 (2H, s); 7.10 (2H, t, J=9.0 Hz); 7.50 (1H, dd, J=5.2 and 9.0 Hz); 7.57 (1H, s); 7.60 (1H, d, J=8.0 Hz); 7.70 (1H, d, J=8.0 Hz).

Workup

  1. temperaturewhile warming to 0° C
  2. additionThen the mixture was poured into ice/saturated ammonium chloride solution
  3. extractionextracted with Et2O (3×100 mL)
  4. washThe organic extracts were washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-0e5be1e8800245c2ae2b545c90adbeb2
Source dataset
uspto-grants-2005_03
Patent number
US06864379B2

Reaction notes

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