4-Hydroxybenzaldehyde → HCID 11492677, compound

HRID 2354286Notes

Reaction equation

HRID 2354286 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19]O)=[O:16])([CH3:13])([CH3:12])[CH3:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 11492677HCID 11492677, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (0.25 g), 2-(tert-butoxycarbonylamino)ethanol (0.33 g) and triphenylphosphine (0.59 g) in tetra hydrofuran (2 mL) was added diethyl azodicarboxylate (40% toluene solution, 1.34 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was directly purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1-3/1) to give 4-[2-(tert-butoxycarbonylamino)ethoxy]benzaldehyde (0.41 g). The title compound was prepared in a similar manner to that described in Reference Example 45 using this material instead of 4-isobutylbenzaldehyde.

Workup

  1. customThe reaction mixture was directly purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1-3/1)

Sources & evidence

ORD record
ord-50814121fb3742a39af652d70cd8ba90
Source dataset
uspto-grants-2010_07
Patent number
US07750145B2

Reaction notes

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