Formic Acid → HCID 10194168, compound

HRID 898656Notes

Reaction equation

HRID 898656 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-a08dbc3c48754f92b67039bd0ae2d970
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

Loading…