Pyridine, hydrofluoride (1:1) → HCID 86602900, compound

HRID 2252500Notes

Reaction equation

HRID 2252500 reaction equation
[Si:1]([O:8][C@@H:9]([CH2:35][C@H:36]([O:63][Si:64]([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:66])[CH3:65])/[CH:37]=[CH:38]\[C@H:39]([CH3:62])[C@H:40]([O:54][Si:55]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56])[C@@H:41]([CH3:53])[CH2:42][CH2:43][CH2:44][O:45][Si](C(C)(C)C)(C)C)[C@H:10]([CH3:34])/[CH:11]=[CH:12]/[CH2:13][O:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=CN=CC=1.F.CCOC(C)=O.CCCCCC>N1C=CC=CC=1>[Si:55]([O:54][C@@H:40]([C@@H:39]([CH3:62])/[CH:38]=[CH:37]\[C@@H:36]([O:63][Si:64]([C:67]([CH3:68])([CH3:69])[CH3:70])([CH3:65])[CH3:66])[CH2:35][C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C@H:10]([CH3:34])/[CH:11]=[CH:12]/[CH2:13][O:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@@H:41]([CH3:53])[CH2:42][CH2:43][CH2:44][OH:45])([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56]

Participants

5

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 21226206Ethyl acetate hexaneHCID 86602901HCID 86602901, compound

Product 1

HCID 86602900HCID 86602900, compoundYield 70,964.203%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The procedure for 36 was used with 67 (1.82 g, 1.77 μmol) and HF-pyridine in pyridine (100 mL) to yield 68 (1.15 g, 71%) by flash column chromatography (EtOAc/Hexane 1:9) as a colorless oil: IR (CHCl3) 3349, 2956, 2929, 2856, 1471, 1448, 1254, 1060, 836, 773, 705 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.58-7.55 (m, 6H), 7.39-7.27 (m, 9H), 5.81-5.65 (m, 2H), 5.56 (t, J=10.7 Hz, 1H), 5.41 (dd, J=11.0, 8.4 Hz, 1H), 4.67 (m, 1H), 4.05 (m, 1H), 3.69-3.63 (m, 4H), 3.53 (m, 1H), 2.73 (m, 1H), 2.52 (m, 1H), 1.64 (m, 3H), 1.58-1.48 (m, 2H), 1.30-1.20 (m, 2H), 1.11 (d, J=6.8 Hz, 3H), 1.10 (d, J=6.6 Hz, 3H), 1.03-0.92 (m, 30H), 0.23-0.14 (m, 18H); 13C NMR (75 MHz, CDCl3) δ 144.3, 134.3, 132.9, 132.0, 128.6, 127.7, 126.8, 86.7, 80.1, 72.3, 66.4, 65.0, 63.1, 42.4, 41.7, 38.2, 35.5, 31.2, 29.5, 26.2, 25.95, 25.89, 19.6, 18.4, 18.1, 18.0, 15.1, 13.3, −2.9, −3.7, −3.8, −4.17, −4.24, −4.3; LRMS (ESI) 937.6 [M+Na]+; HRMS (ESI) calcd for C55H90O5Si3Na 937.5994 [M+Na]+, found 937.6035; [α]20D−10.8 (c 0.84, CHCl3).

Sources & evidence

ORD record
ord-b57bbf871ead478781940e20a57d0b1b
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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