Benzaldehyde → HCID 58342013, compound

HRID 339585Notes

Reaction equation

HRID 339585 reaction equation
[CH3:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]=[C:7]([C:9]3[CH:23]=[CH:22][C:12]([CH2:13]P(=O)(OCC)OCC)=[CH:11][CH:10]=3)[S:8][C:4]=2[CH:3]=1.CC(C)([O-])C.[K+].[CH:32](=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CCCCCC.CCOC(C)=O>C1COCC1>[CH3:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[CH:11][C:12](/[CH:13]=[CH:32]/[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:22][CH:23]=3)[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 13599214HCID 13599214, compoundHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 58342013HCID 58342013, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Prepared as described in the Alkene Formation section using diethyl 4-(6-methylbenzothiazol-2-yl)benzylphosphonate (0.30 g, 0.80 mmol) in dry THF (15 ml), potassium t-butoxide (0.10 g, 0.88 mmol) and benzaldehyde (0.085 g, 0.80 mmol) in dry THF (5 ml) to give the title compound (0.16 g, 60%) as a pale yellow solid after work-up and flash chromatography (2:1 Hexane/EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-eb7aa5ae510848e9acab0cf6f4f4983b
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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