Phthalimide → HCID 57608224, compound

HRID 1171225Notes

Reaction equation

HRID 1171225 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][C:10]=3[CH:11]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:39]1(=[O:49])[NH:43][C:42](=[O:44])[C:41]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]12.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([CH2:16][N:43]4[C:39](=[O:49])[C:40]5[C:41](=[CH:45][CH:46]=[CH:47][CH:48]=5)[C:42]4=[O:44])=[CH:12][C:10]=3[CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 57608269HCID 57608269, compound

Product 1

HCID 57608224HCID 57608224, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (5 mL) solution of (2-(4-fluoro-benzyl)-benzofuran-5-yl)-methanol (83 mg, 0.324 mmol) described in Production Example 76-1-2 were added triphenylphosphine (93.5 mg, 0.356 mmol), phthalimide (52.4 mg, 0.356 mmol) and diethylazodicarboxylate (62.1 mg, 0.356 mmol). This mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain the title compound (81 mg, 65%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-d24b50ba493c469da3b0214c8a36c0fb
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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