Potassium Carbonate → HCID 86718986, compound

HRID 1746266Notes

Reaction equation

HRID 1746266 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.I[CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][C:24]#[CH:25].C([O-])([O-])=O.[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:23]([O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:6][CH:7]=1)[C:24]#[CH:25]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2756771N-Boc-4-hydroxyanilineHCID 86718987HCID 86718987, compound

Product 1

HCID 86718986HCID 86718986, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To tert-butyl 4-hydroxyphenylcarbamate (1.675 g, 8.01 mmol) in DMF (53.4 mL) was added 3-(2-(2-iodoethoxy)ethoxy)prop-1-yne (2.034 g, 8.01 mmol) and K2CO3 (3.32 g, 24.02 mmol). The mixture was stirred at 60° C. for 4 hours followed by the addition of saturated sodium bicarbonate. The mixture was then extracted with ethyl acetate twice, dried over MgSO4, filtered, and then concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% ethyl acetate/heptane) giving tert-butyl 4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)-phenylcarbamate (I-7a: 1.91 g, 71%) as a colorless oil. LC-MS (M-tBu+1) 280.1, t=1.31 minute.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate twice
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (0-40% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-1e191c1ec3874259abf24eb7af760e6f
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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