Diethyl Ether → 1a,2,7,7a-Tetrahydronaphtho[2,3-b]oxiren-3-ol

HRID 437044

反応式

HRID 437044 の反応式
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([OH:22])[C:21]2[CH2:20][CH:19]=[CH:18][CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1.CCOCC.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[O:9]1[CH:19]2[CH:18]1[CH2:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:22])[C:21]=1[CH2:20]2

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 974665,8-Dihydro-1-naphtholHCID 516892Sodium Bicarbonate

生成物 1

HCID 124457371a,2,7,7a-Tetrahydronaphtho[2,3-b]oxiren-3-ol収率 40.7%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

An amount of 25.0 g of m-chloroperbenzoic acid is added over 10 minutes to an ice-cooled solution of 14.6 g of 5,8-dihydro-1-naphthol (prepared as described in Org. Syn., Coll. Vol. IV. pg. 887) in 225 ml of ethyl acetate. After 16 hours at ambient temperature the slurry is poured into a cooled, stirred mixture of 300 ml each of ether and 10% sodium bicarbonate. After 15 minutes the organic phase is separated, washed with water, saturated salt solution and dried. Solvent removal gives an oil which is triturated with two 100 ml portions of boiling hexane. The residue is recrystallized from 150 ml of 1:1 hexane-ethyl acetate to give 6.6 g of 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol, melting point 143°-146° C. Two further recrystallizations of a small sample give the analytical sample melting point 149.5°-151° C.

後処理

  1. additionAfter 16 hours at ambient temperature the slurry is poured into a cooled
  2. customAfter 15 minutes the organic phase is separated
  3. washwashed with water, saturated salt solution
  4. customdried
  5. customSolvent removal
  6. customgives an oil which
  7. customis triturated with two 100 ml portions of boiling hexane
  8. customThe residue is recrystallized from 150 ml of 1:1 hexane-ethyl acetate

出典と根拠

ORDレコード
ord-c034390053d940d4a6987a75d58dc3b2
出典データセット
uspto-grants-1977_06
特許番号
US04029676

関連ノート

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