Formic Acid → HCID 10194168, compound

HRID 1583062Notes

Reaction equation

HRID 1583062 reaction equation
C([O:5][C:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([C:18]2[CH:19]=[C:20]3[C:25](=[C:26]([C:28]#[CH:29])[CH:27]=2)[O:24][C:23]([CH3:31])([CH3:30])[CH2:22][C:21]3([CH3:33])[CH3:32])=[O:17])=[CH:11][CH:10]=1)=[O:7])(C)(C)C.C(O)=O>O1CCOCC1.O>[C:6]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]([C:18]2[CH:19]=[C:20]3[C:25](=[C:26]([C:28]#[CH:29])[CH:27]=2)[O:24][C:23]([CH3:31])([CH3:30])[CH2:22][C:21]3([CH3:33])[CH3:32])=[O:17])=[CH:13][CH:14]=1)([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 12137003HCID 12137003, compound2×

Product 1

HCID 10194168HCID 10194168, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 8-ethynyl-2,2,4,4-tetramethyl chroman-6-carboxylic acid 4-tert-butoxycarbonylmethyl-phenyl ester (Compound 27, 1.5 g, 3.34 mmol) in 1,4-dioxane (30 mL) was treated with formic acid (200 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. The product was further purified by recrystallization from 10-20% ethyl acetate in hexane (1.32 g, 100%).

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-8dbf7d48090f470a9eee9085d4efd9d8
Source dataset
uspto-grants-2004_05
Patent number
US06740676B2

Reaction notes

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