Tetrahydrofuran → HCID 86761887, compound

HRID 1261873Notes

Reaction equation

[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3C(=CC(Br)=[CH:9][CH:10]=3)[C:5]([CH2:31][CH2:32][CH:33]([CH3:45])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:44])[CH2:38][CH2:39][CH2:40][CH:41]([CH3:43])[CH3:42])([CH2:16][CH2:17][CH:18]([CH3:30])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:4]=2[CH:3]=1.C([Li])CCC.C(N1CCCCC1)=O.[CH2:59]1[CH2:63][O:62][CH2:61][CH2:60]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:12]([C:11]3[CH:10]=[CH:9][C:59]([CH:63]=[O:62])=[CH:60][C:61]=3[C:5]2([CH2:31][CH2:32][CH:33]([CH3:45])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:44])[CH2:38][CH2:39][CH2:40][CH:41]([CH3:43])[CH3:42])[CH2:16][CH2:17][CH:18]([CH3:30])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:13][CH:14]=1

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 174291-Piperidinecarboxaldehyde

HCID 86761888HCID 86761888, compound

HCID 178418339Butyllithium

Product 1

HCID 86761887HCID 86761887, compoundYield 72%

Procedure

2,7-Dibromo-9,9-bis(3,7,11-trimethyldodecyl)fluorene (Example 7; 21.02 g, 28.25 mmol) was reacted with n-butyllithium (1.6 M, 16.5 mL, 26.4 mmol) in THF at −78° C., and quenched with N-formyl piperidine (4.7 mL, 42.3 mmol). The crude product was chromatographed over silica gel eluting with 15 and 25% toluene-heptane to get the aldehyde product as a liquid, 13.11 g (72% Yield). Mass spec: m/z 692, 694 (M+). Anal Calcd for C44H69BrO: C, 76.16%; H, 10.02%; Br 11.51%. Found: C, 76.39%; H, 9.85%; Br, 11.49%. 1H NMR (CDCl3), δ ppm: 0.51-0.54 (m 4H), 0.67 (tt, 6H), 0.77 (tt, 6H), 0.85 (d, 12H), 0.92-1.26 (m, 30H), 1.47-1.53 (m, 2H), 1.98-2.02 (m 4H), 7.50-7.65 (m, 3H), 7.79-7.87 (m, 3H), 10.05 (s, 1H).

Workup

customThe crude product was chromatographed over silica gel eluting with 15 and 25% toluene-heptane

Sources & evidence

ORD record: ord-e1e4e05aa4874666acac47519b388aa5
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471035B1

Reaction notes

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