Sodium borohydride → HCID 69204538, compound

HRID 898303Notes

Reaction equation

HRID 898303 reaction equation
[BH4-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14](=[O:21])[CH2:13]3)=[CH:11][C:6]=2[O:5][CH2:4]1>C(O)C.C(COC)OC>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C@@H:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C@H:14]([OH:21])[CH2:13]3)=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18683614HCID 18683614, compound

Product 1

HCID 69204538HCID 69204538, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium borohydride (1.5 g) was added in portions with stirring at 10-15° C. to a solution of 3-(benzo[1,3]dioxol-5-yl)-indan-1-one (10 g) in a mixture of ethanol (75 mL) and dimethoxyethane (75 mL). The mixture was stirred at rt for 1 h and then evaporated in vacuo. The resulting oil was treated with water and diethyl ether, and the organic phase was separated and washed with water and 0.1 N HCl, dried (MgSO4) and evaporated in vacuo to give cis-3-(benzo[1,3]dioxol-5-yl)-indan-1-ol as a brown oil (10 g).

Workup

  1. customevaporated in vacuo
  2. additionThe resulting oil was treated with water and diethyl ether
  3. customthe organic phase was separated
  4. washwashed with water and 0.1 N HCl
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-773d2ae671f04d2192e6dd4d0c279af1
Source dataset
uspto-grants-2008_04
Patent number
US07351734B2

Reaction notes

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