1-Iodooctane → HCID 15290418, compound

HRID 1757152Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[C:11]1[O:12][CH2:13][C:14]2([C:24]3[C:19](=[CH:20][C:21]([OH:25])=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)[N:15]=1.I[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CN(C=O)C>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[C:11]1[O:12][CH2:13][C:14]2([C:24]3[C:19](=[CH:20][C:21]([O:25][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)[N:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 64 mg (0.00127 mol) of NaH in 1 mL of DMF at 0° C. was added a partial solution of 200 mg (0.00063 mol) of the product of Step F. The reaction was stirred at 0° C. for 30 minutes. Then, 304 mg (0.00127 mol) of 1-iodooctane was added and stirring continued for an additional 30 minutes at 0° C. The reaction mixture was poured into ice-water and extracted with Et2O. The Et2O extract was washed with brine, dried (MgSO4) and concentrated. The residue was purified by passing through a silica gel column eluting with EtOAc:Hexanes (1:4) to give 240 mg of a clear oil. 1H NMR (CDCl3) d 7.40 (m, 1H), 7.20 (d, 1H), 6.98 (Ab q, 2H), 3.92 (t, 2H), 2.80 (m, 2H), 1.70-2.20 (m, 4 H), 1.20-1.45 (m, 12H), 0.90 (t, 3H).

Workup

stirringstirring
waitcontinued for an additional 30 minutes at 0° C
extractionextracted with Et2O
extractionThe Et2O extract
washwas washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified
washeluting with EtOAc:Hexanes (1:4)

Sources & evidence

ORD record: ord-f42b01514f8d44e0a52d57515d83ab7f
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05444079

Reaction notes

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