Tetrahydrofuran → HCID 43708295, compound

HRID 1776135Notes

Reaction equation

HRID 1776135 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])=[O:10])=[N+]=[N-].C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O>[NH2:1][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])=[O:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 60207713HCID 60207713, compound

Product 1

HCID 43708295HCID 43708295, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3 (13.5 g, 48.7 mmol), THF (100 mL) and water (50 mL) was added triphenyl phosphine (14.05 g, 53.5 mmol). The resulting mixture was stirred at room temperature for 6 hours. The THF and water were removed in vacuo. The residue was dissolved in the minimal amount of dichloromethane and passed through a silica gel pad (50 g) and washed with dichloromethane (500 mL) followed by a 4:1 mixture of dichloromethane-5% ammonia in methanol (500 mL). The appropriate fractions were concentrated and recrystallized from ethyl acetate to yield 6.45 g of 4 as a pale yellow solid.

Workup

  1. customThe THF and water were removed in vacuo
  2. dissolutionThe residue was dissolved in the minimal amount of dichloromethane
  3. washwashed with dichloromethane (500 mL)
  4. additionfollowed by a 4:1 mixture of dichloromethane-5% ammonia in methanol (500 mL)
  5. concentrationThe appropriate fractions were concentrated
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f8ec7f65a43541eb8848a4f1f2aaa7fc
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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