Formic Acid → HCID 10287701, compound

HRID 898681Notes

Reaction equation

HRID 898681 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:16][C:17]([C:19]2[CH:20]=[C:21]3[C:26](=[C:27]([C:29]#[N:30])[CH:28]=2)[O:25][C:24]([CH3:32])([CH3:31])[CH2:23][C:22]3([CH3:34])[CH3:33])=[O:18])[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]([O:11]C(C)(C)C)=[O:10].C(O)=O>O1CCOCC1.C1COCC1.O>[C:9]([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([O:16][C:17]([C:19]2[CH:20]=[C:21]3[C:26](=[C:27]([C:29]#[N:30])[CH:28]=2)[O:25][C:24]([CH3:31])([CH3:32])[CH2:23][C:22]3([CH3:34])[CH3:33])=[O:18])=[CH:3][C:2]=1[F:1])([OH:11])=[O:10]

Participants

6

Reactant 2

HCID 284Formic AcidHCID 69215936HCID 69215936, compound2×

Product 1

HCID 10287701HCID 10287701, compoundYield 74.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 8-cyano-2,2,4,4-tetramethyl chroman-6-carboxylic acid-3-fluoro-4-tert-butoxycarbonylmethyl-phenyl ester (Compound 31, 0.084 g, 0.18 mmol) in 1,4-dioxane (4 mL) and THF (2 mL) was treated with formic acid (15 mL) at ambient temperature. After 2 h, the reaction mixture was diluted with water and extracted with diethyl ether. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product (0.055 g, 74%).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ba79ab2f18264a4f8b000d6c8fc68fcd
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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