4-Hydroxybenzaldehyde → HCID 136060539, compound

HRID 339590Notes

Reaction equation

HRID 339590 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][C:36]([CH:37]=O)=[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:37]/[C:36]4[CH:39]=[CH:40][C:33]([OH:32])=[CH:34][CH:35]=4)=[CH:22][CH:23]=3)[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 13599214HCID 13599214, compoundHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 136060539HCID 136060539, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Prepared as described in the Alkene Formation section using diethyl 4-(6-methylbenzothiazol-2-yl)benzylphosphonate (0.10 g, 0.266 mmol) in dry THF (10 ml), potassium t-butoxide (0.063 g, 0.559 mmol) and 4-hydroxybenzaldehyde (0.033 g, 0.266 mmol) in dry THF (5 ml) to give the title compound (0.061 g, 67%) as a pale orange solid after work-up and flash chromatography (2:1 Hexane/EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c89d767f09754d13b8fd1bab04c49bb2
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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