Benzyl diethyl phosphate → 4-Benzyl-thiophene-3-carbaldehyde

HRID 1363256Notes

Reaction equation

HRID 1363256 reaction equation
P(O[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(OCC)(OCC)=O.[CH:17]([C:19]1[C:20](B(O)O)=[CH:21][S:22][CH:23]=1)=[O:18].ClC1C=CC(CC2SC(C=O)=CC=2)=CC=1>>[CH2:10]([C:20]1[C:19]([CH:17]=[O:18])=[CH:23][S:22][CH:21]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 298808Benzyl diethyl phosphateHCID 4190637(4-Formylthiophen-3-yl)boronic acidHCID 201615005-(4-Chlorobenzyl)thiophene-2-carbaldehyde

Product 1

HCID 596485394-Benzyl-thiophene-3-carbaldehydeYield 46%

Procedure

The title compound was synthesized from diethyl benzyl phosphate (Org. Lett. 2005, 7, 4875-4878) and 4-formylthiophen-3-ylboronic acid using the conditions to synthesize 5-(4-chlorobenzyl)thiophene-2-carbaldehyde (Example 1.1.a). Purification by prep-TLC (10% heptane/DCM, eluting 3×) yielded 4-benzylthiophene-3-carbaldehyde (204 mg, 46%). 1H NMR (400 MHz, CDCl3) δ ppm 4.29 (s, 2H), 6.83-6.86 (m, 1H), 7.20-7.26 (m, 3H), 7.29-7.34 (m, 2H), 8.12 (d, J=3.22 Hz, 1H), 9.98 (d, J=0.73 Hz, 1H).

Workup

  1. customPurification
  2. washby prep-TLC (10% heptane/DCM, eluting 3×)

Sources & evidence

ORD record
ord-31d9fcafd87d4fbe9928e7c098748daa
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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