Triphenylphosphine → HCID 67006731, compound

HRID 1047518Notes

Reaction equation

HRID 1047518 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH:7]1[CH2:22][CH:11]2[CH2:12][O:13][C:14]3[C:19]([C:10]2([S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:9][CH2:8]1)=[C:18]([F:20])[CH:17]=[CH:16][C:15]=3[F:21])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([S:23]([C:10]23[CH2:9][CH2:8][CH:7]([O:6][CH2:5][CH2:4][NH2:1])[CH2:22][CH:11]2[CH2:12][O:13][C:14]2[C:19]3=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])(=[O:24])=[O:25])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 72472700HCID 72472700, compound

Product 1

HCID 67006731HCID 67006731, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

A solution of 8-(2-azido-ethoxy)-10a-(4-chloro-benzenesulfonyl)-1,4-difluoro-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene (110 mg, 0.242 mmol) in 4:1 THF/H2O (5 mL) was treated with Ph3P (127 mg, 0.484 mmol) and the reaction was heated to 60° C. After 16 h, the reaction mixture was cooled to ambient temperature and concentrated in vacuo to remove the THF. The reaction mixture was diluted with saturated aqueous NH4Cl and extracted with CH2Cl2 (3×). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. Flash chromatography (10% MeOH/CH2Cl2) provided the title compound (52 mg, 52%): 1H NMR (CDCl3 400 MHz) δ 7.62 (d, J=8.8 Hz, 2H), 7.49 (d, J=8.8 Hz, 2H), 7.06 (m, 1H), 6.43 (m, 1H), 5.22 (dd, J=10.9, 2.9 Hz, 1H), 4.11 (d, J=11.7 Hz, 1H), 3.51 (m, 1H), 3.41 (m, 2H), 2.98 (m, 1H), 2.88 (br s, 2H,), 2.39 (m, 2H), 1.94 (m, 2H), 1.49 (m, 3H), 1.13 (m, 1H).

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customto remove the THF
  4. additionThe reaction mixture was diluted with saturated aqueous NH4Cl
  5. extractionextracted with CH2Cl2 (3×)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8cd43593cc73483b9810837f61fc2362
Source dataset
uspto-grants-2013_10
Patent number
US08569521B2

Reaction notes

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