Sodium borohydride → Tricyclohexylstannane

HRID 505955Notes

Reaction equation

HRID 505955 reaction equation
C(OCC)C.O.[BH4-].[Na+].[OH-].[CH:10]1([Sn+:16]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C(OCC)C>[CH:23]1([SnH:16]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 9864905CyhexatinHCID 21584184Diethylether water

Product 1

HCID 25729Tricyclohexylstannane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture (400 mL) of diethyl oxide:water 1:1 was cooled at 0° C. under nitrogen in a three-necked flask of 1 L. Sodium borohydride (3 g, 79.4 mmol) and then tricyclohexyltin hydroxide (30 g, 62.2 mmol) were successively and carefully added. After addition of 100 mL of diethyl oxide, the mixture was stirred 2 days at room temperature. After separation, the organic layer was dried over magnesium sulphate and evaporated under reduced pressure. The crude product was distilled under high vacuum to afford, a colourless oil (23.23 g; 63 mmol).

Workup

  1. additioncarefully added
  2. customAfter separation
  3. dry with materialthe organic layer was dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. distillationThe crude product was distilled under high vacuum
  6. customto afford

Sources & evidence

ORD record
ord-2a62d50584ef47e08d734ce440f27d56
Source dataset
uspto-grants-2010_08
Patent number
US07781610B2

Reaction notes

Loading…