Heptane → 1-[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl][5-(3-hydroxypropyl)-1,3-dihydro-2H-isoindol-2-yl]methanone

HRID 632564Notes

Reaction equation

HRID 632564 reaction equation
[CH2:1]([O:8][C:9]1[CH:23]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([C:32]([CH3:34])=[CH2:33])=[CH:20][C:10]=1[C:11]([N:13]([CH2:17][C:18]#[CH:19])[CH2:14][C:15]#[CH:16])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:35]([OH:40])[CH2:36][CH2:37][C:38]#[CH:39].CCCCCCC>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:23]=[C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:21]([C:32]([CH3:34])=[CH2:33])=[CH:20][C:10]=1[C:11]([N:13]1[CH2:17][C:18]2[C:15](=[CH:16][CH:39]=[C:38]([CH2:37][CH2:36][CH2:35][OH:40])[CH:19]=2)[CH2:14]1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8900HeptaneHCID 793464-Pentyn-1-ol2×HCID 581575202,4-Bis-benzyloxy-5-isopropenyl-N,N-di-prop-2-ynyl-benzamide

Product 1

HCID 866864181-[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl][5-(3-hydroxypropyl)-1,3-dihydro-2H-isoindol-2-yl]methanoneYield 39.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-bis-benzyloxy-5-isopropenyl-N,N-di-prop-2-ynyl-benzamide (0.545 g, 1.21 mmol) in ethyl acetate (10 mL) was added 4-pentyn-1-ol (0.30 mL, 3.2 mmol) and RhCl(PPh3)3(0.161 g, 0.17 mmol). Solvent was removed under vacuum, and the mixture stirred at room temperature overnight. Additional 4-pentyn-1-ol (2.5 mL, 26 mmol) and RhCl(PPh3)3 (0.155 g, 0.17 mmol) were added and the mixture stirred for 48 hours. The mixture was loaded onto a silica gel column and eluted with 7:3 ethyl acetate:heptane to yield the desired product (0.254 g, 39% yield). LC/MS: m/z 534.25 [M+H]+

Workup

  1. customSolvent was removed under vacuum
  2. stirringthe mixture stirred for 48 hours
  3. washeluted with 7:3 ethyl acetate

Sources & evidence

ORD record
ord-3c24c13026ed4c60bb7a8a65f9e8a14f
Source dataset
uspto-grants-2016_04
Patent number
US09321718B2

Reaction notes

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