Ethyl Acetate → 8-Isopropyl-2,2,4,4-tetramethyl-chroman-6-carboxylic acid 4-(2-benzyloxycarbonyl-vinyl)-phenyl ester

HRID 2377352Notes

Reaction equation

HRID 2377352 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:18]([OH:20])=[O:19])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]2([CH3:17])[CH3:16])([CH3:3])[CH3:2].[CH2:21]([O:28][C:29](=[O:39])[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.CN(C)CCCN=C=NCC.C(OCC)(=O)C>ClCCl.CN(C)C1C=CN=CC=1.CCCCCC>[CH2:21]([O:28][C:29]([CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][C:35]([O:19][C:18]([C:6]2[CH:7]=[C:8]3[C:13](=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]3([CH3:17])[CH3:16])=[O:20])=[CH:34][CH:33]=1)=[O:39])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 211072578-Isopropyl-2,2,4,4-tetramethyl-chroman-6-carboxylic acid2×HCID 566275053-(4-Hydroxy-phenyl)-acrylic acid benzyl ester

Product 1

HCID 690737328-Isopropyl-2,2,4,4-tetramethyl-chroman-6-carboxylic acid 4-(2-benzyloxycarbonyl-vinyl)-phenyl esterYield 83%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A solution of 8-isopropyl-2,2,4,4-tetramethyl-chroman-6-carboxylic acid (Intermediate 34, 0.05 g, 0.18 mmol) and 3-(4-hydroxy-phenyl)-acrylic acid benzyl ester (described in Journal of Natural Products, 1990, 53 (4), p821-824, Bankova V., 0.046 g, 0.18 mmol) in anhydrous dichloromethane (5 mL) was treated with 4-(dimethylamino)pyridine (0.052 g, 0.27 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.044 g, 0.36 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then subjected to flash column chromatography using 20% ethyl acetate in hexane as the eluent to afford the title compound as a white solid (0.076 g, 83%).

Workup

  1. customthe resulting reaction mixture

Sources & evidence

ORD record
ord-b1fb4bbe7e6e4c9f8f91905ee8676d52
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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