Sodium Chloride → HCID 12245806, compound

HRID 1066689Notes

Reaction equation

HRID 1066689 reaction equation
C([Li])CCC.[OH:6][CH2:7][C@@H:8]1[C@@H:12]([CH2:13][OH:14])[O:11][C:10]([CH3:16])([CH3:15])[O:9]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[Cl-].[Na+]>O1CCCC1>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:14][CH2:13][C@@H:12]2[C@@H:8]([CH2:7][OH:6])[O:9][C:10]([CH3:16])([CH3:15])[O:11]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 73974-Toluenesulfonyl chlorideHCID 78524473346-74-4HCID 178418339Butyllithium

Product 1

HCID 12245806HCID 12245806, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

21.7 mmol of n-butyllithium (1.59 molar in n-hexane, 13.6 ml) were added at -78 C to a solution of (4R,5R)-4,5-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane (3.32 g, 20.5 mmol) in 60 ml of tetrahydrofuran ((4R,5R)-4,5-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane was prepared according to J. Org. Chem. 33 (1968), page 2171). After stirring for 10 minutes, a solution of p-toluenesulfonyl chloride (4 g, 21 mmol) in 20 ml of tetrahydrofuran which was cooled to −78° C. was added. After stirring at −78° C. for 15 minutes, the mixture was warmed to 20° C. and poured into 200 ml of concentrated sodium chloride solution. The organic phase was separated off and the aqueous phase was extracted twice with 50 ml of ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on 400 g of silica gel using ethyl acetate and n-hexane in the weight ratio 60:40 as eluent. 74.6% of (4R,5R)-[5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]methyl p-toluenesulfonate were obtained ([α]D19=+11.80 (c=1.88 in trichloromethane); cf. J. Org. Chem. 55 (1990), page 4417: [α]D21=+11.30 (c=2.70 in trichloromethane)).

Workup

  1. additionwas added
  2. stirringAfter stirring at −78° C. for 15 minutes
  3. customThe organic phase was separated off
  4. extractionthe aqueous phase was extracted twice with 50 ml of ethyl acetate
  5. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on 400 g of silica gel

Sources & evidence

ORD record
ord-bd98d10b040244759efdc2ed1395ca0e
Source dataset
uspto-grants-2001_06
Patent number
US06245328B1

Reaction notes

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