Salicylaldehyde → HCID 136060540, compound

HRID 339589Notes

Reaction equation

HRID 339589 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+].[OH:32][C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1[CH:35]=O.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:35]/[C:34]4[CH:37]=[CH:38][CH:39]=[CH:40][C:33]=4[OH:32])=[CH:22][CH:23]=3)[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6998SalicylaldehydeHCID 13599214HCID 13599214, compoundHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 136060540HCID 136060540, compoundYield 60%

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 (25 ml), potassium t-butoxide (0.19 g, 1.68 mmol) and 2-hydroxybenzaldehyde (0.097 g, 0.80 mmol) in dry THF (10 ml) to give the title compound (0.16 g, 60%) as a yellow solid after work-up and flash chromatography (1:1 Hexane/EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-be5a38215d5c44bf87ac71c782072809
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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