Triphenylphosphine → HCID 71093170, compound

HRID 332662Notes

Reaction equation

HRID 332662 reaction equation
[N:1]([CH:4]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:5]1[CH:6]=[C:7]([CH:22]=[C:23]([Br:25])[CH:24]=1)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:21][CH2:20][CH2:19][O:18]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[O:18]1[CH2:19][CH2:20][O:21][CH:17]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:6]=[C:5]([CH:4]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH2:1])[CH:24]=[C:23]([Br:25])[CH:22]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 71093444HCID 71093444, compound

Product 1

HCID 71093170HCID 71093170, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred reaction of 2-(8-(3-(azido(phenyl)methyl)-5-bromophenoxy)octyl)-1,3-dioxolane (1.19 g, 2.45 mmol) in tetrahydrofuran (15 mL) and water (0.3 mL), was added triphenylphosphine (0.71 g, 2.69 mmol). The reaction mixture was heated to 60° C. for 16 hours. The reaction mixture was cooled, concentrated and purified by silica gel chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford impure title compound as a colourless oil (0.77 g, 68%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography
  4. washeluting with 0-100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-8e5222325cfb4828bf4d3625a607d1b7
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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