Tetrahydrofuran → 2-(5-Hydroxy-2,4,6,7-tetramethyl-3,4-dihydro-benzo[1,2-b]furan-2yl)ethyl 2-(6-methoxy-2-naphthyl)propionate

HRID 482512Notes

Reaction equation

HRID 482512 reaction equation
[OH:1][C:2]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:5]2[O:6][C:7]([CH2:10][CH2:11][OH:12])([CH3:9])[CH2:8][C:4]=2[C:3]=1[CH3:17].[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[C:26](C(C)C(O)=O)=[CH:25][CH:24]=[CH:23]2.CN(C1C=CC=CN=1)C.Cl.CN(C)CCCN=C=NCC.[O:56]1C[CH2:59][CH2:58][CH2:57]1>C(OCC)(=O)C>[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]=[C:25]([CH:58]([CH3:59])[C:57]([O:12][CH2:11][CH2:10][C:7]1([CH3:9])[O:6][C:5]3=[C:13]([CH3:16])[C:14]([CH3:15])=[C:2]([OH:1])[CH:3]([CH3:17])[CH:4]3[CH2:8]1)=[O:56])[CH:24]=[CH:23]2

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 218852-DimethylaminopyridineHCID 903236-Methoxynaphthyl-alpha-methylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 143438172-(5-Hydroxy-2,4,6,7-tetramethyl-2,3-dihydrobenzo[1,2-b]furan-2-yl)ethanol

Product 1

HCID 677127422-(5-Hydroxy-2,4,6,7-tetramethyl-3,4-dihydro-benzo[1,2-b]furan-2yl)ethyl 2-(6-methoxy-2-naphthyl)propionateYield 74.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(5-hydroxy-2,4,6,7-tetramethyl-2,3-dihydrobenzo[1,2-b]furan-2-yl)ethanol (1.30 g, 5.51 mmol) and 6-methoxy-α-methyl naphthaleneacetic acid (Aldrich, 1.39 g, 6.06 mmol) was stirred in the presence of dimethylaminopyridine (0.67 g, 5.51 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (1.06 g, 5.51 mmol), in tetrahydrofuran (25 mL). The reaction mixture was stirred at ambient temperature under nitrogen for 24 hours, diluted with ethyl acetate (150 mL), washed with water (2×40 mL) and then brine (30 mL). The organic extract was dried (sodium sulfate) and concentrated in vacuo. The residue was subjected to flash chromatography (silica gel, 100-50:0-50, v:v, hexanes:ethyl acetate), and the appropriate fractions were combined to give 1.84 g (74.5% yield) of a foam residue. Fractional crystallization and recrystallization from methylene chloride-hexanes gave 0.40 g (13.0% yield) of white solid.

Workup

  1. washwashed with water (2×40 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03580f09a8a24c4e89ccf5cd91018870
Source dataset
uspto-grants-1998_08
Patent number
US05798356

Reaction notes

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