Cesium carbonate → HCID 68108607, compound

HRID 2179443Notes

Reaction equation

HRID 2179443 reaction equation
[C:1]([O:4][CH:5]1[CH2:19][CH2:18][C:8]2[O:9][C:10]3[C:15]([Cl:16])=[CH:14][C:13](Br)=[CH:12][C:11]=3[C:7]=2[CH2:6]1)(=[O:3])[CH3:2].[C:20]1([S:26]([O-:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].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>C1(C)C=CC=CC=1>[C:1]([O:4][CH:5]1[CH2:19][CH2:18][C:8]2[O:9][C:10]3[C:15]([Cl:16])=[CH:14][C:13]([S:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:28])=[O:27])=[CH:12][C:11]=3[C:7]=2[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2723840Benzenesulfinic acid, sodium saltHCID 68109110HCID 68109110, compound

Product 1

HCID 68108607HCID 68108607, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of the product of step B (230 mg, 0.66 mmol), sodium benzenesulfinate (132 mg, 0.80 mmol), di-palladium-tris(dibenzylideneacetone) (60 mg, 0.07 mmol), cesium carbonate (322 mg, 0.99 mmol) and xantphos (76 mg, 0.13 mmol) was suspended in anhydrous toluene (4 mL). The reaction flask was purged with argon and heated at 110° C. for 5 h. After cooling, the reaction mixture was diluted with dichloromethane and filtered through a celite bed. The filtrate was concentrated in vacuo and the residue purified by flash column chromatography (SiO2, 7:3 hexanes/ethyl acetate) to give a single enantiomer of 6-chloro-8-(phenylsulfonyl)-1,2,3,4-tetrahydrodibenzo[b,d]furan-2-yl acetate (150 mg, 56%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.01-7.92 (m, 3H), 7.83 (d, J=1.8 Hz, 1H), 7.61-7.48 (m, 3H), 5.36-5.28 (m, 1H), 3.06-2.73 (m, 4H), 2.28-2.09 (m, 2H), 2.05 (s, 3H).

Workup

  1. customThe reaction flask was purged with argon
  2. temperatureAfter cooling
  3. additionthe reaction mixture was diluted with dichloromethane
  4. filtrationfiltered through a celite bed
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue purified by flash column chromatography (SiO2, 7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7d2c3bcfabd743a3b45b5c2f438bb91c
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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