Thiophenol → HCID 13714036, compound

HRID 1690690Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][C:6]2([CH3:14])[CH3:13].C1(S)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][C:6]2([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 220 °C

Procedure

In a microwave reaction tube, a mixture of 5-methoxy-3,3-dimethyl-indan-1-one (880 mg, 4.63 mmol), benzenethiol (510 mg, 4.63 mmol), and potassium carbonate (64 mg, 0.46 mmol) in NMP (5 mL) is purged with N2. The reaction mixture is heated at 220° C. for 30 min under microwave irradiation. The reaction mixture made to alkaline with 1N aqueous NaOH (10 mL) and extracted with Et2O (3×20 mL). The aqueous part is acidified in an ice bath with 6N HCl and extracted with Et2O (3×20 mL). The combined organic phases are washed with brine and dried over Na2SO4. After concentration, the crude product is purified with silica gel column chromatography (30% ethyl acetate in hexanes) to afford 5-hydroxy-3,3-dimethyl-indan-1-one as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.63 (d, 1H, J=8 Hz), 6.88 (d, 1H, J=2 Hz), 6.84 (dd, 1H, J=2, 8 Hz), 6.14 (s, 1H), 2.59 (s, 2H), 1.40 (s, 6H), ESMS m/z 177.1 (M+H+).

Workup

customIn a microwave reaction tube
customis purged with N2
extractionextracted with Et2O (3×20 mL)
customThe aqueous part is acidified in an ice bath with 6N HCl
extractionextracted with Et2O (3×20 mL)
washThe combined organic phases are washed with brine
dry with materialdried over Na2SO4
concentrationAfter concentration
customthe crude product is purified with silica gel column chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-85eebe63ed914c28b17278e966390805
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153671B2

Reaction notes

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