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3-Thiocresol → 6-[(3-Methylphenyl)sulfanyl]-1,2,3,4-tetrahydronaphthalen-1-one

HRID 63630
Notes
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Reaction equation

HRID 63630 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1)(=O)=O.[CH3:20][C:21]1[CH:22]=[C:23]([SH:27])[CH:24]=[CH:25][CH:26]=1.CCN(C(C)C)C(C)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH3:20][C:21]1[CH:22]=[C:23]([S:27][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]3)[CH:24]=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 79303-ThiocresolHCID 81531DiisopropylethylamineHCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 1185977176-[(3-Methylphenyl)sulfanyl]-1,2,3,4-tetrahydronaphthalen-1-oneYield 110%

Reagents, catalysts & solvents 3

HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 312751,4-DioxaneSolvent

Procedure

The suspension of 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (1.8 g, 6.1 mmol), 3-methylbenzene-1-thiol (0.76 g, 6.1 mmol), Pd2(dba)3 (142 mg, 0.153 mmol), Xantphos (177 mg, 0.306 mmol) and DIEA (1.58 g, 12.2 mmol) in 1,4-dioxane (60 mL) was stirred at reflux overnight under N2. The reaction was filtered and concentrated. Purification by silica gel chromatography (PE:EtOAc=5:1) gave 1.8 g (100%) of the title compound as an orange oil. [M+H] Calc'd for C17H16OS, 269. Found, 269.

Workup

  1. temperatureat reflux overnight under N2
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-728e7a341e764f538ab3f60ccd3d628b
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447046B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes