Pyridine → (S)-6-Benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol methanesulfonate

HRID 26779Notes

Reaction equation

HRID 26779 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:25])=[C:11]2[C:16](=[C:17]([CH3:20])[C:18]=1[CH3:19])[O:15][C@:14]([CH3:24])([CH2:21][CH2:22][OH:23])[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].N1C=CC=CC=1.C.C(OC1C(C)=C2C(=C(C)C=1C)O[C@](C)(CCO)CC2)C1C=CC=CC=1>C1C=CC=CC=1>[CH3:26][S:27]([O:23][CH2:22][CH2:21][C@:14]1([CH3:24])[CH2:13][CH2:12][C:11]2[C:16](=[C:17]([CH3:20])[C:18]([CH3:19])=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:10]=2[CH3:25])[O:15]1)(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 11067787HCID 11067787, compoundHCID 70588933HCID 70588933, compound

Product 1

HCID 54156209(S)-6-Benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol methanesulfonate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 0.5 g. (1.47 mmoles) of (S)-(-)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol and 0.25 ml. (0.37 g.; 3.2 mmoles) of methanesulfonyl chloride in 5 ml. of anhydrous pyridine was kept at 0° C. for 45 hours then poured into 100 ml. of ice-water and the resulting mixture was stirred for 15 minutes. The mixture was then extracted three times with ether and the combined ether extracts were washed with cold 1 N aqueous HCl followed by water and saturated brine. After drying and filtration, the ether extracts were concentrated in vacuo giving 0.587 g. (95.6%) of (S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ethanol methane as a colorless solid, m.p. 81°-83° C.; [α]25D-0.36° (c 0.82, C6H6).

Workup

  1. additionthen poured into 100 ml
  2. extractionThe mixture was then extracted three times with ether
  3. washthe combined ether extracts were washed with cold 1 N aqueous HCl
  4. customAfter drying
  5. filtrationfiltration
  6. concentrationthe ether extracts were concentrated in vacuo
  7. customgiving 0.587 g

Sources & evidence

ORD record
ord-f83c7d66660141078d1628d50ff5589c
Source dataset
uspto-grants-1979_04
Patent number
US04151205

Reaction notes

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