Carbon Tetrachloride → HCID 86714029, compound

HRID 576312Notes

Reaction equation

[Br:1][C:2]1[C:12]([Cl:13])=[C:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)[CH:10]=[C:9]([C@H:24]2[C@H:29]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:28]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@H:27]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C@@H:26]([CH2:54][O:55][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[O:25]2)[C:3]=1[O:4][CH2:5][CH2:6]CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:82]([Cl:86])(Cl)(Cl)Cl>CC#N>[CH2:47]([O:46][C@H:27]1[C@H:28]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C@@H:29]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C@H:24]([C:9]2[CH:10]=[C:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH3:23])=[CH:19][CH:20]=3)[C:12]([Cl:13])=[C:2]([Br:1])[C:3]=2[O:4][CH2:5][CH2:6][CH2:82][Cl:86])[O:25][C@@H:26]1[CH2:54][O:55][CH2:56][C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a suspension of bromide 29 (1.47 g, 1.59 mmol) in CH3CN (25 mL) were added triphenylphosphine (1.1 g, 3.98 mmol) and CCl4 (2.5 mL) at r.t. The mixture was stirred at 55° C. for 3 hours. The reaction mixture was cooled to r.t and concentrated in vacuo. The residue was purified using normal phase column chromatography to provide the desired product 29-1 (1.03 g, 70%).

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-54e0787ec29e468fbcdf8e616e0bbf2c
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034921B2

Reaction notes

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