Dicyclohexylcarbodiimide → HCID 69687087, compound

HRID 1070395Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([OH:14])=[O:13].[CH3:15][Si:16]([CH3:21])([CH3:20])[CH2:17][CH2:18]O.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.C1COCC1.CN(C)C1C=CN=CC=1>[CH3:15][Si:16]([CH3:21])([CH3:20])[CH2:17][CH2:18][O:13][C:12]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[OH:1])=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-hydroxynaphtoic acid (2.02 g, 10.7 mmol) in dichloromethane (45 mL) and THF (2 mL) were added 2-trimethylsilylethanol (4.6 mL, 32.2 mmol) and 4-dimethylaminopyridine (1.07 g, 8.9 mmol) under N2. The mixture was cooled to 0° C. and 1,3-dicyclohexylcarbodiimide (2.33 g, 11.3 mmol) was added. After removal of the ice bath, the mixture was stirred for 3 h at room temperature. 2N HCl was added to adjust the pH to 2, and the mixture was filtered to remove urea. After the separation of layers the organic phase was washed with water and brine, dried (Na2SO4), and concentrated to dryness. Purification by chromatography gave 2.92 g of 2-hydroxy-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester.

Workup

customAfter removal of the ice bath
addition2N HCl was added
filtrationthe mixture was filtered
customto remove urea
customAfter the separation of layers the organic phase
washwas washed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated to dryness
customPurification by chromatography

Sources & evidence

ORD record: ord-43b2f5c91b0c43b89fb95dcde4bff127
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903086B2

Reaction notes

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