Phenol → HCID 44180964, compound

HRID 1042036Notes

Reaction equation

Br[C:2]1[C:6]2[O:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:9][C:10](=[O:11])[C:5]=2[S:4][CH:3]=1.[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.N12CCCN=C1CCCCC2.[O:54]1CCC[CH2:55]1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd]>[O:15]1[CH2:16][CH2:17][N:12]([C:8]2[O:7][C:6]3[C:2]([C:55]([O:24][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:54])=[CH:3][S:4][C:5]=3[C:10](=[O:11])[CH:9]=2)[CH2:13][CH2:14]1

Participants

Conditions

Temperature: 125 °C

Procedure

A 2 mL conical microwave vial was charged with a magnetic stirring bar, 3-bromo-5-morpholino-7H-thieno[3,2-b]pyran-7-one (103) (50 mg, 158 gmol), phenol (22 mg, 237 gmol), molybdenum hexacarbonyl (42 mg, 158 μmol), trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium (II) (4 mg, 4.7 μmol), tri-tert-butylphosphonium tetrafluoroborate (2.8 mg, 9.5 μmol), tetrahydrofuran (0.5 mL), and 1,8-diazabicyclo[5.4.0]undec-7-ene (71 μL, 474 gmol). The reaction mixture was sealed, and the reaction mixture was magnetically stirred and heated via microwave irradiation to 125° C. for 6 minutes to give phenyl 5-morpholino-7-oxo-7H-thieno[3,2-b]pyran-3-carboxylate (73).

Workup

additionA 2 mL conical microwave vial was charged with a magnetic stirring bar
customThe reaction mixture was sealed

Sources & evidence

ORD record: ord-fae8c129754947dcb5c371b8e5a8da70
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557807B2

Reaction notes

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