Tetrahydrofuran → HCID 69893030, compound

HRID 2121231Notes

Reaction equation

HRID 2121231 reaction equation
C[N:2]([C:4]1[CH:12]=[C:11]([C:13]([O-])=O)[CH:10]=[CH:9][C:5]=1[C:6]([O-:8])=[O:7])C.C1C[O:19][CH2:18]C1.[CH3:21]C(C[AlH]CC(C)C)C>CCOCC>[CH3:21][O:8][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([CH2:13][CH2:18][OH:19])=[CH:12][C:4]=1[NH2:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 131724343HCID 131724343, compound

Product 1

HCID 69893030HCID 69893030, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of dimethylaminoterphthalate (3.07 g, 14.7 mmol) in 30 mL of a 2:1 mixture of THF: Et2O at −78° C. was added neat DIBAL (6.27 g, 44.1 mmol, 3.0 eq.) and the reaction was warmed to 0° C. over 4 hours. The reaction was quenched with 5 mL of methanol followed by 5 mL of saturated aqueous sodium tartrate. The mixture was stirred overnight and then was taken up in ethyl acetate. The layers were separated and the ethyl acetate layer was washed with saturated aqueous NaHCO3and brine and then dried over Na2SO4, filtered and evaporated to an oil. Purification by chromatography on silica gel (50% ethyl acetate-hexane) gave the desired compound (1.03 g, 39%) of 1b as a colorless oil.

Workup

  1. customThe reaction was quenched with 5 mL of methanol
  2. customThe layers were separated
  3. washthe ethyl acetate layer was washed with saturated aqueous NaHCO3and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to an oil
  7. customPurification by chromatography on silica gel (50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-6758629f3ccd4aa8821d41d7579a5fc0
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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