Hexane → HCID 58730928, compound

HRID 1994207Notes

Reaction equation

[Li]CCCC.CCCCCC.Br[C:13]1[CH:14]=[C:15]2[CH:21]=[CH:20][N:19]([Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:16]2=[N:17][CH:18]=1.[Sn:29](I)([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33]>C1COCC1.C(OCC)(=O)C>[C:25]([Si:22]([CH3:24])([CH3:23])[N:19]1[C:16]2=[N:17][CH:18]=[C:13]([Sn:29]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:30][CH2:31][CH2:32][CH3:33])[CH:14]=[C:15]2[CH:21]=[CH:20]1)([CH3:28])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: -78 °C

Procedure

To 2.5 M n-BuLi in hexane (0.67 mL, 1.69 mmol) in THF (5 mL), cooled to −78° C., was added a solution of 26 (0.25 g, 0.80 mmol) in THF (1.0 mL) dropwise. The solution was stirred at −78° C. for 10 min then a solution of Bu3SnI (446 mg, 0.96 mmol) in THF (0.5 mL) was added in one portion. The reaction mixture was stirred at −78° C. for 1 h then at room temperature for 2 h, then poured onto a mixture of ethyl acetate/saturated aq. NaHCO3. The aqueous phase was extracted with more ethyl acetate (2×). The combined organic solutions were dried (MgSO4) and concentrated to give stannane 42 as a light orange oil (483 mg, 115%); 1H NMR (400 MHz, CDCl3) δ 0.71 (s, 6H), 0.98 (t, J=7.4 Hz, 9H), 1.02 (s, 9H), 1.15-1.70 (m, 18H), 6.56 (d, J=3.5 Hz, 1H), 7.26 (d, J=3.5 Hz, 1H), 8.01 (d, J=1.4 Hz, 1H), 8.33 (d, J=1.4 Hz, 1H).

Workup

stirringThe reaction mixture was stirred at −78° C. for 1 h
waitat room temperature for 2 h
extractionThe aqueous phase was extracted with more ethyl acetate (2×)
dry with materialThe combined organic solutions were dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-6928828685c04991a5803fa98b73ad43
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652137B2

Reaction notes

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