Triphenylphosphine → HCID 178443932, compound

HRID 1603310Notes

Reaction equation

HRID 1603310 reaction equation
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].[F:23][C:24]1[C:29]([F:30])=[C:28]([CH2:31][CH2:32][C@H:33]2[CH2:38][CH2:37][C@H:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:35][CH2:34]2)[CH:27]=[CH:26][C:25]=1[C:44]1[N:49]=[CH:48][C:47](O)=[CH:46][N:45]=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:23][C:24]1[C:29]([F:30])=[C:28]([CH2:31][CH2:32][C@H:33]2[CH2:34][CH2:35][C@H:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:37][CH2:38]2)[CH:27]=[CH:26][C:25]=1[C:44]1[N:45]=[CH:46][C:47]([O:16][CH2:15][C@H:14]([F:13])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:48][N:49]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10855629(R)-(+)-2-fluorooctanolHCID 10993240HCID 10993240, compoundHCID 178444400HCID 178444400, compound

Product 1

HCID 178443932HCID 178443932, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

--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 1085, and 900; δ 0.80-1.03 (10H, m), 1.06-1.45 (16H, m), 1.55 (4H, m), 1.82 (6H, m), 2.71 (2H, t J 8, ArCH2), 4.22 (2H, dd, 3JHF 22 and J 4, OCH2), 4.86 (1H, d of sext, 2JHF 48 and J 4, CHF), 7.01 (1H, ddd, J 7.5, 7 and 1.5, 5'-H), 7.67 (1H, ddd, J 7.5, 7 and 1.5, 5'-H) and 8.53 (2H, s, 4- and 6-H); m/z 518 (M+), 489, 475, 461, 447, 365 and 353.

Workup

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

Sources & evidence

ORD record
ord-baacf50b1cae426f934ced85b5e9df81
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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