Dimethyl Sulfide → (R,E)-4-(2-naphtylthio)-3-buten-2-ol

HRID 1004496Notes

Reaction equation

HRID 1004496 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]/[CH:12]=[CH:13]/[C:14](=[O:16])[CH3:15].C1(C2(C3C=CC=CC=3)OB(C)N3CCC[C@@H]23)C=CC=CC=1.CSC.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]/[CH:12]=[CH:13]/[C@H:14]([OH:16])[CH3:15]

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 25517Ammonium ChlorideHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 18795139(E)-4-(2-naphthylthio)-3-buten-2-one

Product 1

HCID 15888161(R,E)-4-(2-naphtylthio)-3-buten-2-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

(E)-4-(2-naphthylthio)-3-buten-2-one (228 mg, 1.0 mmol), (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2] oxazaborol (28 mg, 0.1 mmol) and MS4A (500 mg) were dried by a vacuum pump, followed by substituting with an argon gas. Dry toluene (5 ml) and dimethylsulfide (0.22 ml, 3.0 mmol) were added thereto and, after ice cooling, a solution of borane dimethylsulfide complex in toluene (1.07M, 0.65 ml, 0.7 mmol) was dropwise added. After stirring for two hours, an aqueous saturated ammonium chloride solution was added, followed by filtering through a cotton plug.

Workup

  1. filtrationby filtering through a cotton plug

Sources & evidence

ORD record
ord-31a9fc193d74402ebbf85a5650406951
Source dataset
uspto-grants-2000_04
Patent number
US06049009

Reaction notes

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