Water → HCID 59608934, compound

HRID 1047471Notes

Reaction equation

HRID 1047471 reaction equation
Br[C:2]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:17])[CH:6]2[O:15][CH3:16].[Li]CCCC.[CH2:23]1[O:25][CH2:24]1.O>C1COCC1>[C:11]([C:9]1[CH:8]=[C:7]2[C:3]([CH2:4][CH:5]([CH3:17])[CH:6]2[O:15][CH3:16])=[C:2]([CH2:23][CH2:24][OH:25])[CH:10]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6354Ethylene OxideHCID 59608879HCID 59608879, compoundHCID 178418339Butyllithium

Product 1

HCID 59608934HCID 59608934, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-110 °C

Procedure

To a solution of 40.0 g (134.5 mmol) of 4-bromo-6-tert-butyl-1-methoxy-2-methylindane in 250 ml of THF 107.7 ml of 2.5 M (269 mmol) n-BuLi in hexanes was added for 20 min at −80° C. This mixture was stirred for 40 min at this temperature, cooled to −110° C., and 11.85 g (269.15 mmol) of ethylene oxide was added by one portion at vigorous stirring. The resulting mixture was stirred for 12 h at room temperature, and then 10 ml of water was added. The organic layer was separated and evaporated to dryness. To the residue 200 ml of water was added, and the crude product was extracted with 3×100 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and evaporated to dryness. The product was isolated by flash chromatography using short column with Silica Gel 60 (40-63 um, d 110 mm, l 90 mm; eluent: hexanes/ether=20/1). Yield 27.58 g (78%) of a ca. 1 to 2 mixture of two diastereomers.

Workup

  1. stirringThe resulting mixture was stirred for 12 h at room temperature
  2. customThe organic layer was separated
  3. customevaporated to dryness
  4. additionTo the residue 200 ml of water was added
  5. extractionthe crude product was extracted with 3×100 ml of dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwas dried over Na2SO4
  8. customevaporated to dryness
  9. customThe product was isolated by flash chromatography
  10. additionYield 27.58 g (78%) of a ca. 1 to 2 mixture of two diastereomers

Sources & evidence

ORD record
ord-9dd929a1a0524f1c8e796f5c688549b3
Source dataset
uspto-grants-2013_10
Patent number
US08569532B2

Reaction notes

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