Triphenylphosphine → HCID 67006731, compound

HRID 564352Notes

Reaction equation

HRID 564352 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-2b4b0a41ad404455bd9411541e4b038e
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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