Benzoate → HCID 86746322, compound

HRID 373421Notes

Reaction equation

HRID 373421 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C1C=CC([C:20]#[C:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[S:28][CH:27]([CH3:32])[CH2:26][C:25]3([CH3:34])[CH3:33])=CC=1)C.[OH-].[K+]>>[CH3:32][CH:27]1[CH2:26][C:25]([CH3:34])([CH3:33])[C:24]2[C:29](=[CH:30][CH:31]=[C:22]([C:21]3[CH:4]=[CH:3][C:2]([C:1]([OH:9])=[O:8])=[C:7]([C:6]#[CH:5])[CH:20]=3)[CH:23]=2)[S:28]1

Participants

4

Reactant 3

HCID 242BenzoateHCID 14797Potassium HydroxideHCID 19105539HCID 19105539, compound

Product 1

HCID 86746322HCID 86746322, compound

Procedure

A mixture of 37 mg (0.102 mmol) of ethyl 4(2,4,4-trimethyl-6-thiochromanyl)-ethynyl]benzoate (Compound 56) and 11 ml of ethanolic potassium hydroxide solution was stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue was taken up with water and then acidified with IN HCl. The mixture was extracted with three portions of ether. The organic extracts were combined and then washed with water and saturated NaCl solution and dried (MgSO4). The solvent was removed in-vacuo to give the title compound as an orange solid PMR (CDCl3): 1.17 (3H, s), 1.26 (3H, d, J=6.3 Hz), 1.34 (3H, s), 1.58 (1H, t, J=13.1 Hz), 1.92 (1H, dd, J=13.1 Hz, 2.4 Hz), 3.33-3.48 (1H, m), 7.20 (1H, d, J=8.1 Hz), 7.21 (1H, s), 7.45 (1H, d, J=8.1 Hz), 7.62 (2H, d, 8.4 Hz), 7.95 (2H, d, J=8.4 Hz).

Workup

  1. customThe solvent was removed in vacuo
  2. extractionThe mixture was extracted with three portions of ether
  3. washwashed with water and saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in-vacuo

Sources & evidence

ORD record
ord-a0d8913ff1a646839c78a2bbca7ee04f
Source dataset
uspto-grants-1992_11
Patent number
US05162546

Reaction notes

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