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4-Hydroxybenzaldehyde → 4-(Thiophen-3-ylmethoxy)-benzaldehyde

HRID 1693970
Notes
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Reaction equation

HRID 1693970 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.[S:22]1[CH:26]=[CH:25][C:24]([CH2:27]O)=[CH:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[S:22]1[CH:26]=[CH:25][C:24]([CH2:27][O:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)=[CH:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 123570Thiophene-3-methanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 436461654-(Thiophen-3-ylmethoxy)-benzaldehydeYield 40.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a tetrahydrofuran (250 mL) solution of diethylazodicarboxylate (16.1 mL, 40.9 mmol) were added 4-hydroxybenzaldehyde (5 g, 40.9 mmol), 3-thiophene methanol (3.86 mL, 40.9 mmol) and PS-triphenylphosphine (29 g, 1.41 mmol/g, 40.9 mmol). This mixture was stirred for 7 hours at room temperature. This mixture was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (3.61 g, 40%).

Workup

  1. concentrationThis mixture was concentrated under a reduced pressure
  2. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-2b991db4a2bd42e885d4a2b5934be392
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158657B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes