Phenol → HCID 9958543, compound

HRID 1060840Notes

Reaction equation

HRID 1060840 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)=[CH:8][C:7]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:6][CH:5]=2.[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:31]([O:36]CC=C)(=[O:35])[C@H:32]([CH3:34])O.[C:40]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[CH2:60][O:61]C(/N=N/C(OCC)=O)=O>ClCCl>[CH3:40][O:30][C:24]1[CH:29]=[CH:28][C:27]([C:60]([N:3]2[C:4]3[C:9](=[CH:8][C:7]([O:19][C:20]([F:21])([F:23])[F:22])=[CH:6][CH:5]=3)[C:10]([CH2:11][C:12]3[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=3)[O:18][C@@H:32]([CH3:34])[C:31]([OH:36])=[O:35])=[C:2]2[CH3:1])=[O:61])=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11083914HCID 11083914, compoundHCID 12052585HCID 12052585, compound

Product 1

HCID 9958543HCID 9958543, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The phenolic indole (4) (50 mg, 0.16 mmole) was dissolved in dichloromethane (2 mL). To the phenol solution was added (S)-allyl lactate (24 mg, 0.19 mmole), triphenylphosphine (50 mg, 0.19 mmole), and diethylazodicarboxylate (DEAD) (0.030 mL, 0.19 mmole) and the reaction was monitored by TLC. Once complete the reaction was purified by silica gel chromatography to give the title compound (44.1 mg, 64%).

Workup

  1. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-aac776fa6e974199869b6cc529bdc110
Source dataset
uspto-grants-2003_02
Patent number
US06525083B2

Reaction notes

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