Potassium Carbonate → Methyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-cyanochroman-4-carboxylate

HRID 1021339Notes

Reaction equation

HRID 1021339 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1F)[O:9][CH2:8][CH2:7][CH:6]2[C:14]([O:16][CH3:17])=[O:15])#[N:2].[OH:18][C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O>[C:26]([O:25][C:23]([C:22]1[CH:21]=[CH:20][C:19]([O:18][C:12]2[CH:11]=[C:10]3[C:5]([CH:6]([C:14]([O:16][CH3:17])=[O:15])[CH2:7][CH2:8][O:9]3)=[CH:4][C:3]=2[C:1]#[N:2])=[CH:31][CH:30]=1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117640tert-Butyl 4-hydroxybenzoateHCID 67080208Methyl 6-cyano-7-fluorochroman-4-carboxylate

Product 1

HCID 67080240Methyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-cyanochroman-4-carboxylateYield 75.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
115 °C

Procedure

A 500 ml flask equipped with a Claisen head and a condenser was charged with oven dried MS 4A powder (14.5 g), methyl 6-cyano-7-fluorochroman-4-carboxylate (14.11 g, 60.00 mmol), tert-butyl 4-hydroxybenzoate (14.57 g, 75.00 mmol), K2CO3 (20.73 g, 150.0 mmol), and 1-methyl-2-pyrrolidinone (120 mL). The mixture was degassed with Argon for 1 hour, then heated to 115° C. for 18 hours. The mixture was cooled to ambient temperature. The mixture was filtered through a CELITE pad and rinsed with EtOAc. The combined filtrates were washed with water. The EtOAc layer was dried over MgSO4, filtered through GF paper, and concentrated to a crude oil. The crude oil was purified on silica gel (EtOAc in hexanes gradient) to provide 18.5 g of the desired compound as semisolid.

Workup

  1. customA 500 ml flask equipped with a Claisen head and a condenser
  2. additionwas charged with oven
  3. customThe mixture was degassed with Argon for 1 hour
  4. temperatureThe mixture was cooled to ambient temperature
  5. filtrationThe mixture was filtered through a CELITE pad
  6. washrinsed with EtOAc
  7. washThe combined filtrates were washed with water
  8. dry with materialThe EtOAc layer was dried over MgSO4
  9. filtrationfiltered through GF paper
  10. concentrationconcentrated to a crude oil
  11. customThe crude oil was purified on silica gel (EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-785bb59c64e2460fb1fab45330d87892
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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