Triphenylphosphine → 2-Fluorooctyloxypyrimidine

HRID 1954508ノート

反応式

HRID 1954508 の反応式
CCOC(/N=N/C(OCC)=O)=O.[F:13][C@H:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][OH:16].O[C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC1C(F)=C(CCCCC)C=CC=1C1N=CC(OC[C@H](F)CCCCCC)=CN=1>C1COCC1>[F:13][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][O:16][C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1

参加物

7

反応物 5

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10855629(R)-(+)-2-fluorooctanolHCID 10993240HCID 10993240、化合物HCID 178517760HCID 178517760、化合物

生成物 1

HCID 232970482-Fluorooctyloxypyrimidine収率 140.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(R)-(31)-2-[2',3'-difluoro-4'-(trans-4"-pentylcyclohexylethyl)phenyl]-5-(2-fluorooctyloxy)pyrimidine 49.-Quantities: DEAD (448 mg, 2.58 mmol) in THF (3 ml), (R)-(+)-2-fluorooctanol (379 mg, 2.58 mmol), hydroxypyrimidine 48 (1.0 g, 2.58 mmol), triphenylphosphine (676 mg, 2.58 mmol). The experimental procedure was as described for compound 34. The crude product was purified by flash chromatography (5 to 7% ethyl acetate-light petroleum) to give the 2-fluorooctyloxypyrimidine 49 (820 mg, 61%) (from EtOH), transitions/° C. K 102.2 N* 128.3 I; [α]D26 -2.4° (c 2.0 in CHCl3); νmax /cm-1 (KBr) 2920, 2845, 1540, 1460, 1435s, 1285 1080, and 900; δ 0.80-1.03 (10 H, m), 1.06-1.45 (16H, m), 1.55 (4H, m), 1.82 (6 H, m), 2.71 (2 H, t J 8, ArCH2), 4.22 (2 H, dd, 3JHF 22 and J 4, OCH2), 4.86 (1 H, d of sext, 2JHF 48 and J 4, CHF), 7.01 (1 H, ddd, J 7.5, 7 and 1.5, 5'-H), 7.67 (1 H, ddd, J 7.5, 7 and 1.5, 5'-H), and 8.53 (2 H, s, 4- and 6-H); m/z 518 (M+), 489, 475, 461, 447, 365 and 353.

後処理

  1. customThe crude product was purified by flash chromatography (5 to 7% ethyl acetate-light petroleum)

出典と根拠

ORDレコード
ord-70067792ec954eb283b38557edefbf2b
出典データセット
uspto-grants-2000_09
特許番号
US06121448

反応ノート

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