9-Chloro-9-phenyl-9H-xanthene → 4-Nitrophenyl 4-[(9-phenyl-9-xanthyl)oxy]butyrate

HRID 1456907Notes

Reaction equation

HRID 1456907 reaction equation
COC1C=CC([C:7]([O:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=2)=[O:27])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11](OC)=[CH:10][CH:9]=2)=CC=1.C1C=CC(C2(Cl)C3C(=CC=CC=3)[O:53][C:52]3[C:47]2=[CH:48][CH:49]=[CH:50][CH:51]=3)=CC=1.COC1C(OC)=C(C=CC=1)C(Cl)(C1C=CC=CC=1)C1C=CC=CC=1>CCOC(C)=O>[C:16]1([C:7]2([O:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][C:29]3[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=3)=[O:27])[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[O:53][C:52]3[C:51]2=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 1706559-Chloro-9-phenyl-9H-xantheneHCID 223521854-Nitrophenyl 4-(4,4'-dimethoxytrityloxy)butyrateHCID 66624882Dimethoxytrityl chloride

Product 1

HCID 221021834-Nitrophenyl 4-[(9-phenyl-9-xanthyl)oxy]butyrateYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This compound was synthesized using the same method used to synthesize 1a except that pixyl chloride (PxCl) was substituted for dimethoxytrityl chloride, to give 1b in 80% yield, mp 130°-130.5° C. (EtOAc). 1H NMR (CDCl3) δ 1.98 (m, 2H, H3), 2.7 (t, J=7.3 Hz, 2H, H2), 3.0 (t, J=5.8 Hz, 2H, H4), 7.0-7.5 (m, 15H, ArH), 8.2 (d, J=7.1 Hz, 2H PhNO2 m-H). 13C NMR (CDCl3) δ 25.0 (C3), 31.5 (C2), 61.8 (C4), 75.4 (CPh3), 116.3, 123.2, 123.5, 126.4, 126.6, 127.9, 129.1, 129.4, 148.9, 151.3 (Px C), 122.4, 125.1, 145.2, 155.4 (PhNO2C), 171.0 (CO2). Anal. Calcd for C29H23NO6 : C, 72.3; H, 4.8; N, 2.9. Found: C, 72.0; H, 4.4; N, 3.2.

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-e914971187fc4d23bc34ba8945e1eeb2
Source dataset
uspto-grants-1998_12
Patent number
US05846728

Reaction notes

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