4-Toluenesulfonyl chloride → HCID 86598545, compound

HRID 13925Notes

Reaction equation

HRID 13925 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([CH2:18][CH:19]([OH:22])[CH2:20][OH:21])=[CH:16][C:15]([CH3:23])=[C:14]2[C:10]=1[CH2:11][CH2:12][CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O:21][CH2:20][CH:19]([OH:22])[CH2:18][C:17]2[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]3[C:14](=[C:15]([CH3:23])[CH:16]=2)[CH2:13][CH2:12][CH2:11]3)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68583645HCID 68583645, compound

Product 1

HCID 86598545HCID 86598545, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (±)-3-[4-(benzyloxy)-7-methyl-2,3-dihydro-1H-inden-5-yl]propane-1,2-diol (9.12 g, 0.029 mol) in anhydrous pyridine (290 mL) cooled to 0° C. was added p-toluenesulfonyl chloride (5.84 g, 0.031 mol) and the reaction mixture was allowed to stir for at 0° C. 12 h. The reaction mixture was quenched by the addition of water (10 mL) and the reaction mixture was allowed to stir at room temperature for 15 min. The reaction mixture was diluted with ethyl acetate (800 mL) and washed with aqueous hydrogen chloride (4×1000 mL, 2.0 N), water (500 mL), saturated aqueous sodium chloride (500 mL), dried (magnesium sulfate), and the solvent was removed in vacuo to afford (±)-3-[4-(benzyloxy)-7-methyl-2,3-dihydro-1H-inden-5-yl]-2-hydroxypropyl 4-methylbenzenesulfonate as a crude solid. Treatment of the tosylate with palladium on carbon (10 wt. %, 1.50 g) generally according to the procedure described for Intermediate 11 provided (±)-2-hydroxy-3-(4-hydroxy-7-methyl-2,3-dihydro-1H-inden-5-yl)propyl 4-methylbenzenesulfonate. Treatment of the phenyl with triphenylphoshine (10.17 g, 0.039 mol) and diethylazodicarboxylate (6.75 g, 0.039 mol) generally according to the procedure described for Intermediate 12 gave 9.44 g (91%) of (±)-(5-methyl-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methyl 4-methylbenzenesulfonate as a white solid. Rf=0.62 (silica, ethyl acetate:hexanes 1:4); mp 61-64° C.; Anal. calcd. for C20H22O4S: C, 67.01; H, 6.19. Found: C, 67.02; H, 6.15.

Workup

  1. custom12 h
  2. customThe reaction mixture was quenched by the addition of water (10 mL)
  3. stirringto stir at room temperature for 15 min
  4. additionThe reaction mixture was diluted with ethyl acetate (800 mL)
  5. washwashed with aqueous hydrogen chloride (4×1000 mL, 2.0 N), water (500 mL), saturated aqueous sodium chloride (500 mL)
  6. dry with materialdried (magnesium sulfate)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ffbe5c36a80f4cda84733210d3506cae
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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