Triphenylphosphine → HCID 10993240, compound

HRID 1603301Notes

Reaction equation

HRID 1603301 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][CH2:33][CH2:34][CH3:35])[CH:27]=[CH:26][C:25]=1[C:36]1[N:41]=[CH:40][C:39](O)=[CH:38][N:37]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:23][C:24]1[C:29]([F:30])=[C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:27]=[CH:26][C:25]=1[C:36]1[N:37]=[CH:38][C:39]([O:16][CH2:15][C@H:14]([F:13])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:40][N:41]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10855629(R)-(+)-2-fluorooctanolHCID 196090982-(2,3-Difluoro-4-pentylphenyl)-5-pyrimidinol

Product 1

HCID 10993240HCID 10993240, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

--DEAD (470 mg, 2.70 mmol) in THF (3 ml) was added dropwise via syringe to a stirring solution of (R)-(+)-2-fluorooctanol (396 mg, 2.70 mmol), the hydroxypyrimidine 33 (750 mg, 2.70 mmol) and triphenylphosphine (707 mg, 2.70 mmol) in THF (10 ml) under nitrogen at ambient temperature for 15 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (3 to 5% ethyl acetate-light petroleum) to give the 2-fluorooctyloxypyrimidine 34 (610 mg, 55%) (from MeOH), m.p. 74.7° C.; [α]D25 -3.6° (c 2.7 in CHCl3); νmax /cm-1 (KBr) 2950, 2920, 1575, 1545, 1460, 1440, 1280, 1210, 1130, 1080 and 995; δ 0.90 (6H, overlapping t, Me), 1.26-1.93 (16H, m), 2.70 (2H, t, ArCH2), 4.22 (2H, dd, 3JHF 22 and Jvic 4, OCH2), 4.87 (1H, d of sext, 2JHF 49 and J4, CHF), 7.02 (1H ddd, J7.5, 7 and 2, 5'-H), 7.6 (1H, ddd, J7.5, 7 and 2, 6'-H) and 8.55 (2H, s, 4- and 6-H); m/z 408 (M+), 365, 351, 291, 278, 250 and 221.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography (3 to 5% ethyl acetate-light petroleum)

Sources & evidence

ORD record
ord-7315e597595e45e89620c149389a41ea
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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